The Roleplayers

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The Roleplayers Page 5

by Sophie Stern


  “In the guest room,” she said. “We could turn it into a schoolroom without a lot of hassle.”

  “Do we have to do the pigtails-and-glasses thing?” Kayla asked.

  Anne laughed. “Duh. I did say schoolgirl fantasy, right?”

  Snuggling deeper into the pillows and soft blankets on Anne’s bed, Kayla thought momentarily about just spending the night here. Everything was soft, warm, and cozy. She felt safe, warm, and perfect. Most of all, she felt at home.

  And now she was going to have the chance to experiment with her best friend. Not only would it be Anne’s first time with Bruce, but it would be Kayla’s first time in a threesome. She had never been morally opposed to trying one, but she also hadn’t had the chance to try it out on her own.

  Now she was going to, and her pussy got wet again just thinking about it.

  There was just one problem: they had to convince Bruce.

  6.

  Bitter Jupiter was as busy as it always was when Anne and Kayla waltzed in. It was Wednesday night and they were dressed to the nines, at least for this type of establishment. The bouncer nodded to Kayla, obviously remembering her unusual appearance the week before. She had come to Bitter Jupiter without realizing exactly what type of bar it was, and her teensy weensy dress hadn’t gone over the way she thought it would.

  Tonight, she knew better.

  Tonight, she was a slutty schoolgirl.

  Bruce was sitting at the bar, right where he usually was, dressed in his favorite costume: a mummy. Kayla bit her lip as she remembered wanting to peel away the layers of fabric in order to slide his cock into her mouth. Bruce had been both gentle and passionate during their night together, making her cum and forcing her to experience sex in a new way.

  Now she wanted to try something new.

  And she wanted him to be there.

  He looked up as the girls slid onto barstools on either side of him. Seemingly surprised, he cocked his head to the side and greeted them.

  “Hello, ladies.”

  “Hi Bruce,” Anne practically purred, sliding her hand onto his leg.

  He looked at her hand, then at her, then back at her hand, then simply asked, “What are you playing at?”

  “I’m not,” she said. “I have a proposition.”

  “Oh?” Then he looked at Kayla and smiled. “Told her I was good, did ya?”

  She couldn’t help but blush slightly. She absolutely had told Anne how good he was. She hadn’t left out a single detail, not even the fact that she was dying to have him again.

  She just had to convince him.

  Bruce had a lot to offer. He’d been going to Bitter Jupiter for years. The bar was known for its unusual clientele: no one came without a costume.

  The bar tonight was filled with pirates, princesses, a dinosaur, and even a couple of bears. There was one girl dressed like a slutty nurse and even a girl dressed like a scientist. She was surrounded by sexy zombies. Kayla wondered what that was going to be like.

  “I did,” Kayla said. “And now she wants to go for a ride.”

  Bruce shot a questioning look at Anne, who simply shrugged.

  “Is that really something you want to do?” He asked. “It could ruin our friendship.” It was a legitimate concern and Kayla thought it was good that Bruce addressed it. Having sex would definitely change their relationship, and maybe not for the better. Then again, it might open up a whole new world for Anne, and that's what the girls were counting on.

  “Eh,” Anne looked at him right in the eyes. “We aren’t that close of friends.”

  Bruce laughed and then asked what the girls had in mind. Anne leaned in and whispered to him, letting her tongue graze his cheek softly as she made her way up to his ear.

  “We’re hot for teacher.”

  “I know you don’t usually mix things up,” Kayla quickly added, not wanting Bruce to feel like they didn’t respect his own preferences. “But we were wondering if you’d maybe make an exception…you know, for Anne.”

  He took a sip of his drink and seemed to be thinking about it. Kayla wondered what thoughts were racing through that head of his. Bruce wasn’t exactly the kind of guy who was going to just sit by and let two schoolgirls seduce him. He was always in full control. That was sort of his thing.

  So Kayla was a little surprised when he put his glass down and said, “Sure. What the hell?”

  “Eek!” Anne shrieked, jumping up and down. Her breasts nearly bounced out of her tiny white top as she did.

  Kayla noticed.

  Bruce noticed.

  Almost everyone at the bar noticed.

  “When should we do this thing?” Kayla asked, hoping for sooner, rather than later. She felt like she was pretty brave most days, but was a little nervous about getting cold feet.

  “Now,” Bruce said, motioning the bartender that he was ready to pay his tab.

  “Now?” Kayla looked at him. But he wasn’t in the right costume. Did he even have something that looked like a teacher’s outfit?

  As if reading her mind, he told Kayla not to worry. “I’ll be at Anne’s in half an hour. You girls had better be ready for me.”

  7.

  “What if he doesn’t come?” Kayla sat nervously on Anne’s couch, wondering what they would do if he didn’t show. So far, it had been exactly 34 minutes since they’d seen Bruce. He could be anywhere.

  “He’s going to cum,” Anne told her. “You can count on that. I might not know Bruce as intimately as you do, but I know my way around a dick. He’s going to cum, you’re going to cum, we’re all going to cum.”

  Kayla was too nervous to laugh at her friend’s joke.

  She was too nervous for just about anything at this point.

  “Calm down,” Anne pressed her hand firmly into Kayla’s thigh. Sliding it up beneath her skirt, she reminded Kayla of their playtime the other day. “You’re going to be amazing.”

  Kayla took a deep breath. Anne was right. There was nothing to be nervous about. After all, she’d been with Bruce and she’d been with Anne. Now the only thing left to do, naturally, was to be with both of them together. It wasn’t weird. It was going to be fine.

  “I need a drink,” Kayla told Anne honestly.

  With a quick jaunt into the kitchen, Anne produced two very strong rum-and-cokes for the duo to drink.

  “To good friends and bad choices,” Anne said as they clinked their glasses together.

  Kayla downed her drink, immediately feeling more relaxed at the thought of what was going to happen. Everything was going to be okay. They were all going to be fantastic.

  A knock sounded at the door, and Anne put her drink down.

  “I wonder who it could be,” she said with a wink as she hurried to the front door. Kayla followed close behind.

  Anne yanked the door open.

  Bruce stood before them in a pair of khaki pants and a long-sleeve button down. The top button was undone, revealing just a smidge of his bare chest. He held a ruler in his hands and he was smiling mischievously.

  “Kayla,” he said, staring at her until her knees felt weak. She felt his piercing eyes take her all in from the top of her head to the tip of her toes. His eyes lingered when they ran past her heaving cleavage.

  Then he turned to Anne.

  “Anne,” he said, giving her the same treatment. Kayla sneaked a glance at her friend and wasn’t surprised to see that she seemed to feel the same way Kayla did: nervous and excited.

  “Bruce,” Anne began to speak, about to invite him inside, but Bruce pushed past her into the house.

  “When you’re in my presence, Anne May,” he said harshly, slapping the ruler against one hand, “You will address me as Mister Colyer. Do I make myself clear?”

  So this was how it was going to work, Kayla realized. Bruce had already fully immersed himself in his character. He was no longer her friend, Bruce. Now he was Mr. Colyer, their teacher. He was going to give them lessons on lust, learning, and how to give good head, but h
e was going to do more than that, Kayla realized. He was going to punish them if they didn’t do a good job.

  Her ass ached for his touch just thinking about him slapping her - hard - with the ruler, and her pussy grew just a little bit wetter as she wondered if he would fuck her before, during, or after he spanked her.

  “I’m sorry, Mr. Colyer,” Anne hurried to say, following him into the living room.

  Kayla closed the door to the house and locked it, then hurried to rejoin her friends.

  “When you asked me to meet with you today, Anne,” Bruce looked at his pupil, “I didn’t realize it was going to be so you could show me disrespect.”

  Anne blushed five shades of red as she bit her bottom lip, unsure of what to say.

  She was freezing.

  Kayla jumped in. “Mr. Colyer,” she said coolly. “I’m sure Anne wasn’t trying to be disrespectful, but I know she’s really sorry.” She shot a glance at Anne, who was still standing still. Why was she so nervous all of a sudden? Kayla was, too, to be sure, but this was Anne. Anne was not Kayla. Anne didn’t get nervous. She didn’t get scared. She didn’t freeze when someone gave her a hard time.

  Then again, she was friends with Bruce. Maybe she didn’t know how to act.

  Bruce opened his mouth to speak, but Kayla continued. “Maybe we should continue this in your office.”

  Bruce cocked an eyebrow, as if to say, “I have an office?” Instead, he simply nodded and followed the girls upstairs to Anne’s guest room.

  When they walked into the room, Bruce looked around, taking everything in. Anne’s desk sat on one side of the room, centered on the wall. The girls had pulled it out so a chair would fit behind it, the way a teacher would sit at a desk in a classroom. They had placed two other chairs in front of it so that the students could sit there for their “talk” with the teacher.

  The other side of the room held a large bed and a dresser that was topped with a variety of textbooks they had hauled up from the bookshelf downstairs. It wasn’t perfect, but it looked more like a classroom now than it did a bedroom.

  Of course, it was obviously a sex classroom.

  And Anne and Kayla had some hard lessons to learn.

  8.

  Bruce walked into the room and sat on the edge of the desk. He motioned with the ruler for Anne and Kayla to take their respective seats, which they did. Kayla's skirt was so short that she could feel the coolness of the chair against her bum. Her pussy twitched as she wondered what Bruce was going to do to them first. He had them at his beck and call. He could do anything.

  He watched both of the girls as they sat quietly with their hands folded in their lap, taking in everything about them. Their pigtails and cropped tops were perfect for their choice of role play. Kayla wondered if his dick was getting hard just thinking about all the different ways he could slide it into them. She wondered if he was going to start out rough and then slow down or if it was going to be the opposite.

  Anything could happen.

  "You've been very naughty, Miss May," Bruce said, finally, standing up. "And I don't take kindly to my students showing me disrespect."

  Anne blushed and looked at her hands. She said nothing.

  "Stand up," Bruce commanded, and Anne obeyed, gingerly smoothing her skirt down. It didn't matter. It was still short enough to show the edges of her white panties.

  "Come here." Anne did as she was told.

  Bruce grabbed her by the arm and pushed her forcefully against the desk, face down, so that her ass was pointed up toward him. He used one hand to push up her skirt and take a good, hard look at her panties.

  "Mmm," he murmured, rubbing his hand across her panties. "That's right, you've been very bad. And do you know what I do to bad girls?"

  "Punish them!" Kayla piped up, perhaps a little too quickly. Bruce shot her a nasty look.

  "Wait your turn and shut your mouth, Miss Hart, or your punishment will be nothing to smile about, I assure you."

  Kayla bit her lip. Bruce was harsh when he was in character, but she felt more turned on than she thought possible as she watched him press himself up against Anne's panties. He placed his hands on her hips, then let them roam up and down her back and he pushed his now-hard cock against her ass. Anne let out a small moan and Bruce smiled before pulling away. As he did, his hands grabbed her panties and brought them to the floor. Now they were around Anne's ankles, and her ass and pussy were exposed to the room. Even from where she sat, Kayla could see that her friend was wet and aching. How was she going to feel after her spanking?

  Kayla didn't have to wait long to find out. It was only a second before Bruce began to rub one cheek with his hand before bringing it swiftly against Anne. She let out a small yelp as he did so. The sting had been sharp, to be sure, but not overly painful. Not yet.

  "This is what happens to bad girls, Anne," Bruce leaned down and bit her ear softly. He whispered something Kayla couldn't understand, but that Anne clearly could because she immediately lifted her ass higher for Bruce to touch again.

  Kayla watched him spank her several times, first with his hand, then softly with the ruler. It didn't take long for Anne to turn a beautiful crimson. Kayla wanted to come over and finger her friend, replaying memories of their last encounter with each other, but she didn't. She knew if she did, Bruce would start spanking her, and it wasn't time for that yet.

  Instead, Kayla reached into her panties and began to softly rub her clit, playing and touching her pussy and enjoying how wet she was. It wasn't often that she got this turned on. Something about the entire situation was so forbidden, exotic, and strange that she just couldn't help herself. She couldn't wait to find out what happened next.

  Bruce noticed Kayla touching herself and stopped spanking Anne to give her a glare.

  "I don't recall giving you permission to touch your pussy, Kayla," he said to her. Kayla immediately pulled her hand away, but it was too late. Bruce was already next to her, yanking her out of the chair by her hair. Kayla let out a whine as Bruce pushed her over the desk and swatted her hard several times. He didn't bother taking her panties off for the first few swats, but then he ripped them off and tossed them aside and continued spanking her. Kayla turned her head and met Anne's eyes. A combination of excitement and confusion played on her face. It stung, but she also knew that Bruce was in control. He had them exactly where he wanted them.

  Kayla felt him pull her hair again, this time pulling backwards so she had to lean her head back. Then his mouth was at her ear and he whispered, "How does it feel, Kayla? How does it feel to finally be the bad girl who needs to be spanked? How did you like your spanking?"

  "I liked it," she mumbled.

  "What did you say to me, Slut?"

  "I liked my spanking very much, Sir," Kayla told him.

  "Good," he said, "but your punishment isn't over." He pulled Kayla up from the desk and looked at her while she simply stood there. She wasn't sure what to do next or what he was going to do, but her ass was stinging from the spanking and her pussy was even more soaked than before. The bulge in his pants let her know that he was just as turned on as she was, even if he didn't let her know. She was more than ready to ride his cock until he was screaming her name, but she knew he wouldn't let her.

  Not yet.

  "Sit down and watch me fuck Miss May," Bruce commanded. Kayla did as she was told, sitting firmly in her chair as Bruce returned to Anne and slipped a finger inside of her.

  "You're wet," he said simply, then unzipped his pants. His cock popped out and he didn't bother taking his pants all the way off before pushing his dick softly against Anne. She moaned loudly and he continued to tease her for a minute.

  "Please," she finally said, "Please."

  "Please?" He asked her. "What? Please what?"

  "Please," she turned her head to meet his eyes. "Please fuck me, Mr. Colyer."

  Bruce pushed her head down against the desk and rammed his dick into her aching slit, meeting Kayla's gaze as he did so. He co
ntinued to fuck Anne, grinding against her again and again as he watched the yearning growing in Kayla's face. It was killing her not to be able to rub herself. It hurt. It ached. She was ready for her turn. She was ready for him to be in her.

  After a moment, Bruce pulled out of Anne. "That's enough," he said. "Return to your seat."

  Anne looked only momentarily confused before she did as she was told. Bruce finished stripping off his clothes and tossed them to the side. Now he looked at Kayla. Instead of speaking, as she thought he would, he simply pointed to her and then to his cock, as if to say, "Come suck it."

 

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