Roll for Initiative Pt. 01 – Erotic Couplings – Free Sex Story

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All characters are adults

Copyright @Planeis Productions

Completely Fictional

Roll For Initiative Ch. 01

Will had spent a good portion of his first 33 years trying his best to hide how much of a nerd he is from most people. His true, close friends, which normally amounted to 1-2 people at a time, he allowed to see it. But even from them, he hid certain things. Like, when he was 17 and really into anime for the first time. He dove deep into it as a hobby for about 18 months before his interest mellowed out and regressed to more of a passing interest. But, during that whole 18 months he never once mentioned it to his close friends because he was afraid of what they would say. Why? Social anxiety? Fear of rejection? Who knows. No one who knew him ever treated him anything other than nice, the only people who treated him badly were the same stupid assholes at school who treated everyone bad. But for whatever reason, he always felt like he needed to hide certain things about his interests from people.

One of the things he had an interest in, but never told anyone about, was tabletop roleplaying games like Dungeons and Dragons. But, because he was shy about his interest, he never played it. Games like that are a social experience, which are very hard to have if you don’t talk to anyone about them. So, his interest always stayed casual. Occasionally he would read about a game, or an update to Dungeons and Dragons rules, or he would see it discussed on social media like twitter or YouTube. But he never mentioned it to his friends and never played himself.

Until now. Finally, as he approached his late 20s, he started to relax a little and open up to people more often. He no longer felt the need to hide everything and was much more open to getting together with people than he ever had been before. Then, one day a few months ago, he was chatting with some work friends and his opportunity arose. He was eating lunch in the cafeteria at work, he worked as a financial planner for an investment firm. A lot of the people he worked with were smart, but also pretty down to earth regular people. One of them, Jane, mentioned that she was watching a TV show where they mentioned Dungeons and Dragons and that she didn’t really understand what it is.

“Like, I get that it’s a game, but I don’t really understand how it’s played.”

None of the others spoke up. Will cleared his throat and said, “Well. I’ve never played personally, but I know how it works. Have you ever played a video game like Zelda or something like that?” Everyone nodded their heads. “Well, Dungeons and Dragons takes place in that type of setting, a fantasy setting with monsters and weird creatures, magic, swords, arrows, right. But in a game like Zelda, the boundaries of what you can do and where you can go are set by the people who designed the game and wrote the software, right? Like once you get to the end of the map in Zelda, that’s it. If you want to make Link do something, if the designers didn’t program that action in, you can’t do it. Well, in Dungeons and Dragons, anything can happen. Same type of setting, you build a character. And the thing that determines the boundaries of what you can do and where you can go is basically determined by the game rules, and by a friend of yours.”

Will just got a bunch of blank stares. Heather spoke up. “A friend?”

“Yes, so one person has to run the game. So, for example if we all decided to play, one of us would be the Game Master or Dungeon Master. So you design a character, we start playing, and if you say, “I want my character to fly through the air,” the game master might say “Ok well, your character isn’t capable of flying, but there are things in the setting we could find that would give you that power.” And then maybe you can try to find them. Stuff like that.”

Will continued while he had everyone’s attention, “And then there’s the roleplaying aspect. So, you all design a character, give it a name, a description, you can design its backstory, whatever you want. Then, when we play the game, maybe your character meets someone from its fictional past and you have a conversation with that person, like maybe… I don’t know, a robber killed your parents like Batman. So you confront them, in character and say what you want to say, and then the Game Master responds back to you. The game master is responsible for playing all the beings who aren’t being played by the other players.”

Jeff said, “I think I get it. So a lot of it is just acting.”

“Yea sort of. There’s rules for battle and rolling dice and stuff to0 which is a big part of it.”

Jane looked transfixed. “I think we should play.”

And now, here they all were. It had taken a few weeks, but eventually they all decided to meet at his house for an introductory game. He had been spending a few hours with everyone helping them design a character and learning a few of the basic rules. Now, they had eaten dinner, he was set up behind his game master screens so they couldn’t see what he was doing and they were spread out at the table around him. Jane, Heather, Jeff, Mark and Tanya.

Will couldn’t believe it. He’d finally gotten people over to his house to play a game, people that he liked, that he thought liked him, and they seemed to be enjoying it. Not only that, but one of them, Jane, looked… stunning. And he’d had a crush on her for the longest time.

Jane had chosen to play a Bard style elf character and had come prepared with a few songs to go along with her bardish nature. Everyone seemed to have picked up the rules fairly easily and were enjoying the game so far. They had one small combat encounter and now they had told Will they wanted to visit a tavern. Pretty simple game that had gone on for about two hours, including a lot of introductions to rules and the players testing things out for themselves.

Will says, “Ok, so after a while you are all pretty drunk and have racked up quite a bill with this bar. What do you do now?”

Jane says (in character as her elf Pixy), “I walk up to the bar and order one more drink, stumbling slightly because of how drunk I am. So I walk up to the bar and ask him how much the bill is, and I kinda toss my long pink hair across my face.”

“Okay, so the bartender looks at the tab, writes down some notes and says ‘You and your friends owe 45 gold pieces.”

Jane (as Pixy) says, “But gee Mr, we don’t have that kind of cash right now. Is there a way I could uhm, earn a discount?… and then I pull down my shirt a little to show off my cleavage.” Jane in real life pulled down her shirt a little and also revealed some more of her impressive cleavage.

Will knew his eyes boggled at the sight of Jane’s chest being more revealed. He’d never seen anything like that around work and hadn’t been expecting it here. As people at the table giggled like children, Will gathered his wits about him again and said in game, “Well, that is an impressive offer. Make a persuasion roll, with advantage.” Will briefly explained to the group how performing a skill like this works with the dice and Jane rolled two twenty-sided dice, both of which were middling rolls.

Wanting to keep a good thing going and keep it fun, Will said, as the bartender, “You’re fun, but 45 gold is quite a bit of cheddar to just be wiped away. I think you’ll need to pay at least 40 and maybe I’ll call the rest even.”

Jane got a mischievous look in her eye and said, “Can my character whisper to the bartender?”

Will was intrigued, “You want to tell the bartender something that the rest of the group can’t hear?”

“Yes.”

“Sure, you can do that.” Will said and waited as Jane got up from the table and walked over to him. He wasn’t sure what to expect, but Jane leaned down and whispered in his ear, in a very breathy way, “I for real want you to touch my body.” And then she stood up and walked away.

No one except him knew what she had said, but they could tell by the look on his face that it was something interesting. As Jane sat down at the table, Will went back to his bartender voice and said, “Alright. I guess y’all are good. And maybe I’ll see you later,” and then he pointed his finger at “Pixy” and winked one eye and everyone laughed.

Then Will laughed and said, “Alright, so that might be a good place to stop for the night. We can say you all got your tabs wiped out and could head up stairs to rest for the evening.” They all started to clean up the game and the food and Will tried his best to casually look Jane over without being noticed.

He had of course noticed that she was a very attractive woman at work, but that was always a much different environment. For one, everyone was dressed very professionally at work, and the atmosphere was much different than being social with a few alcoholic beverages being passed around.

Now, as opposed to wearing her professional attire, she was wearing very flattering bright blue leggings and a red sweatshirt that appeared to be several sizes too large for her. Despite that, he saw hints of her body underneath, combined with what he saw of her at work, made him think she was hiding a very good body under that sweatshirt. And of course he knew she was pretty. He tried to stop himself from smiling, afterall, it was just a game. She had just said that to be funny. Right?

They kept picking up and people started to make their way out. Will noticed that Tanya seemed a little drunk and said, “Hey Tanya, are you OK to drive.” She looked at him embarrassed and said, “uhm. Actually, I’m not sure if I am. I might need to call an Uber, but then, my car would be stuck here.”

They spoke briefly about some options and Will said, “Oh so you live only ten minutes from here. Maybe I could just give you a ride and we can figure something out in the morning. No need to pay for an Uber.”

Will then saw Jane glide over from across the room, “Well maybe I can help. You can drive her car and her back to her house, I could follow and take you back here. That way she has her car and I’ll just leave from here. It’s only a few minutes, no big deal.”

Will wasn’t sure, but he thought he saw … some kind of look between Tanya and Jane. But whatever it was, it was gone in a second. “Alright. It’s fine with me.”

“Oh thanks you guys are the best.” Tanya said.

They all got into the respective vehicles. Will drove Tanya’s car to her house and parked it where she asked and helped Tanya get safely to the door, then met Jane back at her car and got in the passenger seat.

“Ready when you are,” Will said. Jane glanced at him and patted her hand on his thigh, rather close to his crotch in his opinion and said, “That was nice of you to offer that, Will.”

Will gulped hard as her hand was still on his leg and said, “Hey no biggie. Only a few minutes for all of us right?” Jane removed her hand and started driving back to his place.

As they drove, Will looked at her figure in the dim light of the roadway, her face and clothes illuminated by passing streetlights and the glow from her vehicle’s instrument panel. “Did you have fun?”

Jane smiled and said, “Yes I did, it was unlike anything I’ve done for a long time. I enjoyed the uhm, roleplay? You know, the acting as our character part.”

They got a few more streets down the road and Will was still noticing just how striking she was outside of the stuffy office environment. “Yea I think people had fun. I enjoyed playing with the characters too.”

“Oh, did you? Did you like the little show I put on for you?” she smiled and put her hand back on his thigh, even higher up his leg this time. Will could feel his heart start to beat faster as his crotch suddenly felt a lot more… constricted.

Will tried to laugh casually, inside, his head was spinning, “Ha ha yeah… it was fun seeing everyone loosen up and have a different kind of fun. We should do it again sometimes.”

Jane moved her hand back to the steering wheel and pulled in front of his house. Will breathed a sigh of relief as his anxiety level came back down to earth, “Well. Alright, I guess I’ll talk to you all at work.”

“Actually Will, I left my purse inside your house. Do you mind?”

“Oh, no of course not, come on in.”

They both went back into the house and Jane walked over to the table where her purse was hanging over the back of a chair, but he noticed she didn’t pick it up.

“Actually, there was something, I mean it was great and all, but everything was moving so fast I didn’t really get any time to speak with you one on one. I mean you’ve got his nice house and I feel like you didn’t really give us a chance to see it or talk about anything other than the game. Why don’t we have a drink? You know, just the two of us for a few minutes.”

“Oh sure, yea I know what you mean, I did kinda want to talk to people a little more. What would you like? A margarita?” Will said, seeing Jane with another mischievous, or what he believed to be mischief, smile waiting at the table.

“Yes, that would be great!” she smiled and moved over to the couch while he went to the kitchen to start making them a drink. The sounds of him mixing ingredients and opening and shutting drawers looking for a lime squeezer filled the air.

When he walked into the living room he saw his couch, with enough room for 6 people as it formed an L shape, she was sitting on one end. He didn’t sit next to her, but on the other side of the corner from her. Close, but still some separation. He noticed she had rolled the sleeves of her sweatshirt. He thought about what was hiding under her clothes and felt his heart start to race a little. He hadn’t mentally prepared himself to be alone with anyone, let alone someone as gorgeous as Jane.

“So uh, this is the living room I guess,” Will said.

“Yea I see that. I Love what you’ve done with the place. It looks so cozy. You should have people over more often, you’ve obviously got the space.”

“Well,” Will said, taking a big gulp of his drink. “I’d like to, but uhm, I don’t know.”

He noticed Jane finish her drink.

“Like it?”

She laughed, “Sorry, yes. I Love margaritas and this one was just so small.”

“Well, sorry. I followed my favorite recipe. Guess I should have made you a double.”

Again she laughed, this time reaching over and patting his leg again. “Yes, could you please, sorry. It was just really tasty.”

Will took his glass and finished it, might as well make himself another while he’s at it. As he started making more drinks, he asked her, “So what was your favorite part?”

Jane looked at him and said, “Oh I don’t know. I just like trying new things. I thought the rolling during combat was fun, even failing. I liked roleplaying, like we were kids making believe again. And it was fun seeing you kinda take charge and corral the group. I mean, not that you are like, passive at work, but it’s just a different atmosphere. We’ve all got our assigned roles and when it’s time to make a decision we just have some input and let the bosses do their thing. But here, it was like seeing a whole new side of you.”

Will poured them their drinks from the shaker and said, “You liked me kind of being in charge of you.”

Jane smiled another mischievous smile and said, “Well yea, kind of. I like it when people take charge. It’s a uhm… interesting dynamic, sometimes.”

Will still was nervous, but he had decided it was pretty safe to say that at least for now, Jane liked being around him. He gave her the drink he had made. They talked for a few more minutes about how Jane thought everyone else thought about the game. Will noticed that Jane put her hand back on him when he sat next to her and kept moving it to different places. First one thigh, then the other, then his back and shoulder. Will decided to follow her lead and be a little forward himself, placing his hand on her knee as he was laughing at something particularly funny that she said.

“I don’t know. I just thought it was interesting when we would ask if we could do something kind of outlandish and you would find a way to gently tell like, ‘no, that’s not really possible right now.’ And then you would kind of give us some more reasonable options. You were really trying to help us have fun but also keep us from getting too outrageous. A weird kind of leadership role. Like the group dad.”

Will finished his drink and picked hers up, which she had also finished again. He could tell they were both getting a little silly, but at this point he didn’t care. His hormones were absolutely raging and his dick was noticeably cramped in his pants. Before he had gotten up Jane had put one leg over his and put her arms around him and at this point he was considering taking one of the biggest shots with a woman he ever had.

Will had only been with a few women in his life and had never had a serious girlfriend. He certainly didn’t make a habit of making moves on gorgeous girls like Jane. He’d never made an attempt on someone he worked with. The only women he’d been with were a couple one night stands in college that he felt like he’d somehow lucked into, and one random blind date where the woman had made it clear she was borderline desperate to get away from her husband for the night. He hadn’t really felt good about that, but she’d been so upfront about what she wanted that he had felt it would be basically rude to turn her down.

Now, Will was pretty sure he was getting the clearest signals from any woman he’d ever seen, and he was fighting his overall nervousness to make a move. Surely he had to at least come out of this with a plan for a date, right?

Will said, “Do you ever take charge?”

Jane got up from the couch and walked over to the counter where he was making drinks, leaned on the countertop and gave him a full view of her cleavage down her shirt, while casually saying, “Sure sometimes, when I’m out with the girls and they clearly need someone to handle the groups activities. Or uhm… well…. “

Will let that comment hang in the air for a minute while he shook their next round of margarita’s in the shaker. “Well what?”

“Well, I mean, you know. Sometimes I like to uh, take charge uhm…. In the bedroom, maybe.”

Will handed her a drink and said, “Sometimes?”

Jane stopped leaning on the counter, took a sip of her drink and moved a little closer to him, placing her hand on his stomach. “Well, I mean. Yea, sometimes. Most of the time I like it if the man takes charge. It’s freeing to be told what to do.”

Will decided it was now or never. He put his arms around the small of Jane’s back and pulled her close, kissing her. He kissed her hard and pressed her body against his crotch so she could feel how hard he was. He heard her moan lightly as she pressed her body against his.

With one hand he reached up and put it behind her head, pulling her face closer to him and opening his mouth as they both kissed deeper. With the other he reached down to her ample Ass and pulled her body tighter against him, squeezing her butt as their tongues felt each other.

The butterflies were raging in Will’s stomach, but he decided to press on. He was picking up her signals loud and clear. He kissed her for a few more seconds and then moved his hand from behind her head to grope her large tits. She pressed his hand harder to her tit as he grabbed hold. Will decided to press on, moving his hand off her body for a few moments until he slid his hand under her shirt and pressed it back onto her breast, under her bra. She moaned into his mouth as he continued kissing her deeply.

Will pulled back from kissing her and took a deep breath, “Get on your knees.”

For a moment, he thought he’d ruined everything. He’d never been so forward with a woman in his entire life, other than in his fantasies. He’d thought their conversation about how she liked a man to take charge had led to this, but now, looking into her eyes and the surprised look on her face, he was sure this ride was at an end.

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