Pocket Change

by E. M. Leya

  "Do I need anything from the drawer?"

  "Nope. I got it all right here. But you have to promise me if you don't like something, you'll say so. Don't do things just because I thought about trying them. It all comes down to you liking what we do, so don't fake it."

  "I won't, but now you have me very curious. Are you sure you won't let me peek?"

  "Nope. Sorry, but I want Al to enjoy your reaction as much as I will." Andy set the bag on the bed, then he started to undress.

  Jess watched him as he kicked off his shoes and eased out of his pants. He wore a new pair of boxers that weren't too revealing but looked good enough on him. He wanted to surprise Jess by getting almost naked. It was part of his plan to see how Jess reacted to him pushing things a little more intimately between them. He pulled his shirt over his head and set it aside.

  Jess stared. "You're going to do this in your boxers?"

  "Is that okay? I wanted to be comfortable. I've gotten hard the last few times and while the sweatpants weren't horrible, I don't want to end up pressing against the zipper of my jeans the whole time." He liked the way Jess was looking up and down his body and had to will his cock not to react.

  "Yeah, it's fine. I just didn't think you were that comfortable doing this. I'm glad you are."

  "Do these look okay? I know they aren't sexy briefs like you're wearing, but you know I've never been into those." He set the bag on the bed where he could reach it once the camera was on.

  "Yeah, you look fine." Jess grinned. "So you're enjoying this?"

  "I am. I mean, the money helps, but seriously, it's been fun. I like doing this with the two of you. Al's a great guy, and he seems okay with me joining in, so I figured why not get comfortable and enjoy it?" He looked at the computer. "Will the camera pick up all of the top half of the bed?"

  "Yeah, for the most part. It doesn't get the very edges. We can move it if we need to. The farther back I put it, the wider the shot, but the farther it is for Al to see."

  "It should be okay there for what I have planned." He pushed back the nervousness at what he was going to do. He hoped Jess liked it and it didn't go too far. He prayed he knew Jess well enough to know what he could and couldn't get away with. He was putting their friendship on the line if he did everything he had planned.

  "Al already sent payment. I guess he was pretty sure you'd be here with us. Again, I'll get the money to you as soon as I can. You should set up an account on the app so I can just transfer it to you."

  "I don't mind waiting." He'd never liked using money apps if he didn't have to. "Al must be pretty well off to spend a thousand dollars a week on us."

  "I don't know much about him. He's never talked about himself much. When I've asked, he's brushed off the questions, so I just let it go. I have no clue what the guy does." Jess sat down on the bed. "Ready? He'll call any minute."

  "Yeah." He took a deep breath as he leaned back against the pillows. "As ready as I'll ever be."

  "You're nervous. That makes me nervous." Jess glanced at him.

  "Don't be. I think you'll love what I have planned." Andy met his gaze. "Trust me."

  "I do." Jess smiled. "More than I trust anyone else in my life."

  Those words meant a lot to Andy. They'd been through so much together, but tonight could change everything. The computer started to ring and Andy closed his eyes, saying a silent prayer that everything would be okay.

  "Good to see both of you tonight," Al said.

  "You too. Did you have a good week?" Jess asked.

  "I did. But I've been looking forward to tonight. Good to see you, Andy. I'm glad you decided to keep joining us."

  "I've enjoyed being able to do this with you guys." Andy smiled.

  "Did you come up with something good for tonight?" Al asked.

  "I did. I hope you both like it. If you don't, tell me and we'll figure something else out." Andy glanced at Jess. "First, I want to blindfold Jess."

  "Nice." Al laughed.

  Jess sucked in a loud breath.

  "You okay with that?" Andy asked.

  "From the look of his cock, he is," Al pointed out.

  Andy looked down to find Jess rock hard beneath his underwear. "Perhaps you should take those off first, then I'll blindfold you. I need you fully naked for what I'm going to do."

  "You're going to do?" Jess swallowed.

  "Yep." Andy grinned at Jess's sudden nervousness.

  "I'm liking this," Al said.

  "Get undressed, Jess." Andy felt the desire to take control.

  Jess slipped off his underwear and set them next to him on the bed. His cock was hard and already leaking precum.

  "I've never seen him get this turned on so quickly. He must like the idea of being blindfolded," Al said.

  Andy reached in the bag and pulled out a blindfold he'd bought. It was made of soft material, but the lady he'd bought it from assured him that it would keep someone from seeing anything. She'd said she'd used one just like it. "Are you okay with this, Jess?"

  Jess licked his lips. "Yes."

  "Good, then come here and let me put it on you." Andy turned so he could slide the mask over Jess's eyes and make sure he couldn't see.

  "How does it feel, Jess?" Al asked.

  "Good, it's comfortable, but it's scary not being able to see what you guys are going to do."

  "I'm not going to do anything but watch." Al laughed.

  "And I will tell you everything I'm going to do before I do it," Andy assured him. "First, I'm going to cuff your hands behind your back."

  Jess sucked in another heavy breath.

  "Remember, you can say no at any time, and you have a safe word." Andy pulled a pair of cuffs from the bag.

  "Oh, those are nice," Al said. "They are two cuffs, linked together with a chain. The outside of the cuff is leather, the inside looks to be some soft fuzzy stuff. I'm sure you've seen them in pictures."

  Jess nodded.

  "Let me get behind you." Andy moved around Jess, then gently took his hands, and cuffed him so that his hands were trapped against the small of his back. "Does that feel okay?"

  Jess moved his arms for a moment, then nodded. "It's good."

  Andy loved seeing Jess this way. "Okay, up on your knees. I'll help you. I want you at an angle so Al can see your ass, but I can also still reach it without blocking his view."

  "What are you up to?" Al mused.

  "You'll see soon enough." Andy helped Jess turn so he was up on his knees in front of the camera. "Okay, you can lower your chest to the bed. I need your ass in the air."

  "Andy?" Jess asked.

  "Do you trust me, Jess?" Andy knew Jess was nervous, but his cock was still rock hard so he wasn't worried that Jess was in any distress.

  "Yes."

  "Then just relax. This is for your pleasure."

  Jess lowered his chest to the bed.

  Once he was in position, Andy pulled the next two items out of the bag. One was a large bottle of lube, and the other was a wand of anal beads. The latex beads went increased in size from tiny to large. He's gotten the wand instead of the strings so he wouldn't have to touch Jess with his hands very much. The wand was firm enough to use just touching the end of it.

  "Nice choice." Al sounded impressed.

  "Thanks." Andy grinned. "I've never done this, so let me know if I do anything wrong." He took a towel from his bag and put it on the bed, then covered the beads in lube.

  "I'm going to push anal beads inside you, Jess. Are you okay with that?"

  "Fuck." Jess groaned against the mattress. "Yes."

  "Tell me to stop if it hurts." Jess put the lubed tip of the wand against his best friend's hole and gently pushed. Never in a million years did he think he'd be doing something like this, but as Jess's ass opened and the first bead popped inside him, Andy found himself rock hard. He pushed more, watching as three more balls entered him. There were two left, and they were large. "More?"

  "Please," Jess grunted.

 
Andy pushed one more into him, fascinated at how easily Jess's ass stretched around them.

  "Stop there. Leave one out," Al instructed. "Look at how good that ass looks glistening with the lube. Makes me want to fuck it."

  "He does look good like this. I like having control over him this way." Andy ran his fingertips down Jess's spine, causing him to arch, then groan. "You okay, Jess?"

  "I should have never told you my fantasy about being tied up."

  "Want me to release you?" Andy asked.

  "Hell, no."

  Al laughed. "What next?"

  Andy pulled out a small leather riding crop. The lady had told him it was good for beginners because it had a wide bit of leather at the tip that wouldn't hurt as much as some of the thinner crops.

  "Ah, fuck. He's going to love that," Al whispered.

  "I thought he might." Andy ran his hand over the end of it.

  "What?" Jess asked with a nervous squeak to his voice.

  "Well, since you enjoyed the spanking so much, I thought we'd try something new. I bought a riding crop to try on your sexy little ass." Andy ran the tip of the crop over Jess's ass.

  "Look at his cock leak now," Al pointed out.

  Sure enough, there was a wet spot forming on the bed from precum dripping. Andy ran the tip of the crop over Jess's balls. It was tempting to gently smack the underside of his balls with the crop, but he wouldn't do that until he was sure Jess was into that kind of pain. "Do you want this, Jess?"

  "Yes, but if I can't?"

  "You'll let us know if you can't. We stop if you want us to," Andy promised him. He would never push Jess father than he could handle.

  "Okay." Jess's body tensed.

  "Relax. We'll take care of you." Andy trailed the tip of the crop over his skin, teasing him. His own cock pulsed with desire and need. He was more aroused than he'd ever been in his life. It was all he could do not to pull his cock free and stroke himself. Taking a deep breath to refocus, he remembered everything he'd learned from the lady at the store. She was active in the scene and had given him a shitload of information on how to use the crop. He'd enjoyed learning about this stuff so much, he wished he could make a career out of it. This was the kind of education he liked.

  Without warning Jess what was coming, he brought the crop down on his ass hard enough to sting.

  Jess cried out, his back arching.

  Andy didn't wait for him to recover before bringing the crop down on the other cheek. "More?"

  "Yes." Jess groaned.

  Again, Andy used the crop, turned on by the red welts that were starting to show on Jess's pale skin. He longed to reach out and touch the marks he made, but there would be time for that later. He continued with the swats until he'd given Jess four on each ass cheek. "You should see yourself," Andy mused, running the crop softly over the welts.

  "More," Jess cried.

  Worried it would be too much, Andy glanced at the camera.

  "If he wants more, give them to him. Not many. These are going to hurt long after we finish here. We don't want him unable to sit," Al said.

  The comment reminded Andy that Jess had a date with another man tomorrow night. Jealousy rushed through him, hating that Jess would be giving any of his time to someone else. He brought the crop down harder than he had before, causing Jess to cry out, but that only made Andy want to do it again. Jess should be punished for wanting someone else. He swatted him again, then dropped the crop and brought his bare hand down over the marks he'd just made. At the point he was about to lose control, he stepped back, fisting his hands at his side, breathing heavily.

  "Jess?" Al asked. "Are you okay?"

  "Hmm?" Jess mumbled. "Yeah, I'm okay. Was good." He kept his head down, but his cock was still erect and his chest rising and falling in steady breaths.

  Andy stared at Jess's ass, his chest tightening at how red it was. He wasn't sure whether to be aroused or disgusted. It had to hurt, but Jess had asked for more. Where did pleasure and pain meet and when was it too much. According to the lady he'd talked to, a good submissive could take a lot, but it was something that they built up to. Had he taken Jess too far?

  "What do you want now, Jess?" Andy asked.

  "Whatever you want to give me." Jess's voice was soft.

  If only he dared. Andy went to the other side of the bed and took Jess by the shoulders, lifting him so he was kneeling on the bed. He reached out and twisted each nipple hard, enjoying the way Jess's cock jerked at his touch. "You're so fucking responsive." He stared down at Jess's cock and how hard he was. Temptation was too much and he reached down and wrapped his hand around Jess's length. He shuddered at the sound Jess made. "You want to come, but it's not time yet. We aren't finished." He stroked him again, fascinated at the feel of another man in his hand. It was different than when he touched himself. He didn't want to stop, but forced himself to. He pinched Jess's nipples again, drawing out another loud moan, then pushed Jess back down so his chest was on the bed and ass was in the air. "I like having you this way. Love having control over you."

  "Andy…" Jess's voice was like a caress.

  Going back around the bed, Jess reached down and ran his fingers over Jess's welted ass. "Does it hurt?"

  "Yeah, good." Jess moaned.

  "Good." He wanted Jess to remember this moment while he was on his date with that guy tomorrow night. He wanted Jess's mind on him, not the new guy he was going out with. He slid his hand down and cupped Jess's balls. They were heavy and hot against his palm. He rolled them over his fingers, then let them drop, dangling below his weeping cock. "Can you feel the beads?"

  "A little," Jess admitted. "Not as good as getting fucked."

  "How about if I fuck you with them?" Andy asked.

  "Please."

  Andy had gone a lot farther with things than he'd wanted to. He'd never planned on touching Jess the way he had. But now that he'd done it, he wanted more. It would wait. Too much too fast might be an issue. For which one of them, he wasn't sure. Instead of playing with his cock and balls like he wanted, he gripped the handle of the anal bead wand and pulled gently.

  He loved the way Jess groaned as each ball popped free of him. He loved seeing the stretch of his ass around them. He got to where only two balls were left, then pushed it back in, filling Jess up again.

  "Oh, God," Jess cried.

  "Again?"

  "Please."

  Andy did it again, this time faster, then again, and again until he was fucking Jess with the anal beads. He was so turned on. So aroused at everything they'd been exploring. Unable to wait, needing to come now, Andy used his free hand and pushed his boxers down his legs. He gripped his cock in a tight fist and started to stroke.

  "Yes," Al whispered, reminding Andy that they weren't alone.

  Hearing his voice only turned Andy on more, and he pumped his fist up and down his length as he continued to move the beads in and out of Jess's ass. When it got to be too much, he pulled the beads completely from Jess's body, letting them drop on the bed. His hole was open, the clear lube making it glisten. For the first time in his life, Andy had the urge to fuck another man. He couldn't. He wouldn't. But the thought was enough to push his orgasm closer. He moved behind Jess, placing a palm on the small of his back, holding him in place as he continued to stroke his cock in hard, desperate strokes. He was so close, and he knew exactly what he wanted to do. Giving in to his desire, praying Jess wouldn't freak out on him, Andy aimed his cock at Jess's hole and came. Hot ropes of come shot from him, splattering over Jess's ass. The thick white fluid was vivid against the red of his ass cheeks and the pink of his hole, and as he watched his cum drip down the crack and puddle against that hole, Andy knew that he'd never be the same again. He wanted Jess and he doubted anyone, man, or woman, would ever be enough compared to the man in front of him now.

  "That was amazing," Al's voice was breathy. "Did you feel that, Jess?"

  Jess had his head face down against the bed, his breathing coming hard, his body
tense. "I need to come. Please let me come."

  Andy was happy to give him what he needed. Going around, he again pulled Jess up so he was on his knees. He kept his hands cuffed behind his back, but he reached up and gently removed the blindfold from Jess's eyes. When Jess looked up at him, Andy reached down and wrapped his hand around Jess's cock. "If Al says you may come, I'll help you get there."

  Confusion filled Jess's eyes, but then was quickly replaced with desire. "Please. Can I come, Al? Will you let me come?"

  Al laughed. "I think you've earned it. Go ahead, Andy. Give our boy what he needs."

  Stroking another man was harder than he'd thought. He watched Jess's face to see what he seemed to like and what he didn't. He kept his stroke steady, resisting the urge to add a twist to his fist like he would when he did this to himself. His gaze went from watching Jess's cock to meeting his gaze, and once their eyes locked, he couldn't look away. He smiled, enjoying the need in Jess's stare, the desire that filled the room. He loved the way Jess thrust his hips, fucking into his fist. Unable to keep from touching him, Andy reached out with his free hand and twisted one nipple hard. It was enough. Jess cried out, his head falling back, his mouth open in a gasp, as his body tensed and his cock released sending cum all over Andy's hand.

  "Fuck, you're so hot," Andy whispered as he stilled his hand on Jess's cock, but still held him. He waited until Jess had a chance to come back to reality before he pulled his hand free and lifted it to Jess's mouth. "Now clean me off."

  Jess's gaze met his and didn't leave as he sucked each one of Andy's fingers into his mouth and cleaned them.

  Al's voice broke the silence, bringing them both back from the moment they'd been sharing. "You two are fantastic like this. Tonight was everything I knew it could be. I'm looking forward to seeing what happens next. I regrettably have to leave town this week and will miss our usual Friday night call, but I will be back the next week for more. Are you both okay?"

  "Yeah," Andy forced himself to look at the camera. "Be safe on your trip."

  "I will. You take care of Jess tonight. Make sure to get something more than your cum on his ass, okay."

  Jess's eyes flashed up to Andy's face. He stared for a moment, then cleared his throat. "Thank you, Al. I enjoyed tonight."