Pocket Change Read online

  "We'll get there. You're moving up in the company, but you're right, being single will help you save. I can't wait until I graduate and can actually make some money. The day I'm able to quit waiting tables is a day I'll celebrate."

  "I'll celebrate with you." He meant it too. He knew how hard it was for Jess. He'd come from money. Big money. Being disowned had been hard on him. Andy had always been poor, so he was used to struggling and not having a lot, but the last few years had been hard for Jess. Andy did what he could to teach Jess how to live frugally, but he still saw how hard Jess struggled with not being able to get what he wanted when he wanted it. Teaching him to budget hadn't been easy. He hated Jess's parents for what they'd put their son through.

  They sat in silence for a bit, watching the people around them. It was good to just be out. He didn't need to say or do anything around Jess. The two of them were able to sit in comfortable silence without needing to speak. He loved that.

  The food came and Andy focused on his burger, grinning across the table when Jess reached over and stole some of his fries. "I told you to get food."

  "I just wanted a few." Jess tossed a whole fry into his mouth and chewed. "Don't give me that look. I eat more than enough. I get free meals at work. I'm just trying to stay in shape. I'm not running like I used to."

  "You run to school and home every day. That's what, ten miles a day?"

  "Something like that." Jess shrugged. "But I'm sitting on my ass in class all day too. I'm not lucky enough to have a job that builds muscles the way yours does."

  Andy ran his hand down his arm, feeling the strain in his shoulder as he did. "It might build muscle, but I'm always sore. If my mom asks you what I want for my birthday, tell her a hot tub and a sexy masseuse in a string bikini."

  Jess laughed and it was a good sound, one he didn't hear often enough. For a guy who used to be nearly carefree, life had sure turned on him. He wished there were more he could do to cheer him up and help make things easier for him.

  "I can imagine your mother's reaction if I ask her to find you a woman in a bikini."

  "Mom knows I'm not an angel."

  "That doesn't mean she's going to do her part to tarnish what little bit of halo you have left. I know your parents are open-minded, but I'm pretty sure it only goes so far." Jess stole another fry.

  "She'll be glad Beth is gone. She never liked her."

  "That should tell you something."

  "Right, but then again, the only person I've ever brought home they've liked is you. Maybe they just don't want me to find a woman and fall in love."

  "I don't believe that. She's been pushing you for grandchildren too hard for her not to want you to find someone. Maybe you should let her set you up with somebody. Didn't she say her friend had a daughter?" Jess raised a brow.

  "Yeah, no. The last time my mother set me up with someone, it was a disaster. I'm not going through that again. I'm happy staying single for the time being. As much as I hate saying this, Brad will be home soon and she'll be focused on fixing him instead of pushing me to get married. I almost feel sorry for Brad. I can't imagine living at home again."

  "We'll make sure to get Brad out of there from time to time. I love your parents, but you're right, they will obsess over him. Any chance he might get an apartment with you?" Jess asked.

  "I doubt it, but it's not a bad idea. I have to be better to live with than my parents, right? We'll see once he gets home. For now, I'm going to try and forget about Beth and just focus on getting my shit together." It was time to focus on himself for a change and not some woman he had to keep happy. For now, it was going to be all about him. He'd save money and focus on getting what he wanted for a change. There would be time for dating later.

  "You and me both." Jess lifted his mug in salute. "To independence."

  "Independence," Andy repeated. Hoping that somehow the two of them could find it. As long as life didn't keep throwing them curveballs, everything would hopefully come together.

  CHAPTER THREE

  Wearing a tight pair of black underwear, Jess adjusted the pillows on his bed. Beside him, he'd set his large, purple dildo, and a large bottle of lube. The dildo had been intimidating when he'd first got it, and it took a bit of stretching and practice to use it, but he loved it now. He still made sure to stretch himself before he knew he'd be using it, making it less work while he was on camera. Al was the only client he used that dildo with. He was patient enough not to rush Jess while he worked it inside him.

  Jess took a deep breath, relaxing as he prepared for the show he'd need to give Al. He was actually excited. He'd had a hell of a week, even having the last two days off from classes. Work had been hell, and he'd made one mistake after another, on top of dropping a plate of lasagna on a customer's lap. If it could go wrong, it had. He needed a good fucking, and tonight, even if he had to do it to himself, he was going to get one.

  The ring alerted him to Al's call coming in and he hit connect on his computer, smiling at the dark screen. "Hello."

  "Hi," Al sounded cheerful.

  "How are you this week?" Jess asked as he adjusted himself against the pillows.

  "It's been a busy week, but thoughts of tonight got me through it."

  Jess laughed. "Is it horrible to say it was the same for me? I couldn't wait to take your call."

  "Careful or I'll think you enjoy what we do together." Al laughed.

  That was the thing though, they didn't do it together. Al was watching him, but he didn't get to see the pleasure he brought Al. He longed to see the look on his face, the way his body tensed when aroused, even the way he might arch his head back when he came. They didn't share that. And out of all his clients, Jess wanted to share that with Al more than anyone. "I do enjoy what we do. I've never hidden that from you."

  "How many other clients do you have now?" Al asked.

  "It changes week to week. I have four regulars, but I fit a few others in when I have free time. None of them have been with me as long as you have." He stayed still, knowing not to touch himself or start anything until Al asked him to.

  "Each time we talk, I worry you're going to tell me it's the last time." For the first time ever, Al sounded unsure of himself.

  Jess sat up straighter. "No, I have no plans on stopping this. At least with you. There are others I will drop, but not you."

  "Why keep me and not the others?"

  "Because you don't make me feel dirty. Some of the others, well, most of the others, they are sleazy, creepy, and make me uncomfortable. With you, I've never felt that way. I enjoy this with you."

  "Is it because you can't see me?" Al asked.

  "No, I don't think so. It's your voice and in the way you talk to me. You're not like them. If you saw some of the others, you'd understand. Take the dirtiest, slimiest, closeted man you can imagine, then make him even worse. That's what I end up with most of the time."

  "I'm sorry about that. It's not what you deserve. What you do is beautiful. Not something that should ever make you feel dirty." Al sounded as if he was taking a drink, then cleared his throat. "Do you think most are married men? The closeted ones?"

  "I know some are. Twice during a session, I've had their wives walk in and catch them." Jess laughed, even though at the time it had been humiliating, looking back, he could see the humor in it.

  "That must have been interesting. Good thing you insist on payment first." Just as Al said that Jess's phone dinged, alerting him Al's payment came through.

  "Thank you for that. I almost feel guilty about charging you because I enjoy this so much."

  "You need the money, I do not," Al said softly. "You're worth every penny I pay."

  "Thanks." Jess's cheeks heated.

  "Not used to compliments?"

  "Not really. There's no one around to really compliment me."

  "What about Andy?"

  Jess shrugged. "He's my best friend. We trade more playful insults than we do compliments. Don't get me wrong, he'd compliment me
if there was a reason, but you know how friendships are. You get so comfortable with someone, you don't have to say that kind of stuff."

  "You should always say that kind of stuff to a friend," Al insisted. "But I do understand. It is different with a best friend. Even more so than a romantic partner, a best friend is someone you can completely be yourself with."

  "Exactly. That's how it is with Andy. I don't have to worry about him judging me. He already knows the worst about me." Jess laughed, then gave the camera an innocent look. "Not that there is anything bad about me."

  Al laughed. It was a deep sound that he'd never heard before and it made him realize how little he'd ever heard Al laugh or show any real sign of emotion. "None of us are perfect, Jess. Now, how about you slide out of that sexy underwear. You might as well be loosening yourself up while we talk."

  A wave of excitement rushed through Jess and his cock thickened at the thought. It wasn't as good as being fucked by someone else, but it was the next best thing. He eased the underwear down his legs and set them on the bed beside him so they were still in view of the camera.

  "I'm not sure I've ever seen you this hard so quickly in any of our sessions. You're looking forward to this today, aren't you?" Al asked.

  "I am. I thought about it all week. I need to be fucked so badly."

  "And the fact it's with that giant dildo doesn't turn you off?"

  "God, no. It turns me on. I love how it fills my ass. I need the pain, the pleasure. It's a strange mix of both. And to know you're watching me do it gets me hotter. I don't use it with any other client. You're the only one who gets to see the purple one."

  "I'm flattered, but why is that? Why only me?"

  "Because you don't rush me with it. I can take my time with it. Besides, I know how much it turns you on to watch me with it. The only times I've ever heard you sound like you were about to come was when I use the purple dildo. I'm not even sure you do come, but you sound close. Like you're more turned on than other times."

  Al laughed. "Guilty. It's fucking hot as hell to see you stretched around that thick thing. I have to admit, the first time I saw you use it, I didn't think you'd be able to take it."

  Jess blushed, the heat spreading up his neck and over his face. "When I bought it, I was worried I'd wasted the money."

  "I wish I could have watched you use it for the first time." Al's voice was filled with a mix of lust and admiration.

  "It probably wasn't very sexy to watch. I had lube everywhere and every other dildo I own was used to help try and stretch me to take that one. Once I got it in, I just laid there, not moving for like an hour, exhausted, but excited I'd done it."

  "You've come a long way. I love watching you fuck yourself with it. I'm assuming you've already been stretching?"

  "A bit off and on all week, but yes, I've been stretching today so that it won't take as long as last time. I didn't want to make you sit through that."

  "I don't mind. I like watching you. Grab that lube and get started, we can talk while you play," Al commanded.

  "Yes, Sir." Jess reached for the lube. "Can I ask you something personal?"

  "You can ask. It doesn't mean I'll answer."

  Jess smiled. "Fair enough. I was just wondering if you're a top or if you like being fucked the way I do."

  Al was quiet for a moment, then said, "I've done both, but I enjoy topping more than bottoming. For the right man, I'd do both, but if you haven't noticed, I like being in control. There's just something hot about feeling a man beneath me as I plow into him. Do you top?"

  "I like both, but I like being fucked more. It's been so long since I've gotten laid, I've almost forgotten what it's like with someone." Jess eased his lubed finger into his ass, then added a second, working them in and out as he opened himself up.

  "You do fine on your own it seems."

  "I guess you wouldn't be shocked to hear that I love being watched." Jess grinned at the camera.

  "Not surprised at all. Did you ever think about getting into porn?"

  "Nah, I don't have the body for that, and I don't want a bunch of technical stuff going on around me. I'd love to have the camera crew watching, but I'd hate to have to shift positions for camera shots, pause mid-scene to deal with something, and I want to pick who I fuck, not have someone tell me who I perform with. This works for me."

  "Good, because it works for me too."

  Jess focused on what he was doing, stretching his ass wide, shoving three fingers in, and using them to stretch and relax his muscles. He was ready for the dildo, but he never did anything without Al telling him to do it.

  "Your cock is so hard. You really are excited for tonight. The only thing that would make this better is if I were able to push that dildo inside you myself." Al's voice was husky.

  "I'd lose my mind if I could just lay back and enjoy this. Not do the work."

  "I know you would and that would be sexy as hell to watch. I think you're ready for more. Are you stretched enough to go straight to the purple or do you need something smaller first?"

  "I'm ready."

  "Good, then let me see you push that inside you. Take your time. I'm just going to sit here and enjoy the show. Once it's in, just hold it there. Don't fuck yourself with it yet."

  "Yes, Sir." Jess reached for the dildo and poured lube over it, coating it as completely as he could while still able to grasp it tightly at the base. The thing was huge, with a thick head and shaft that equaled the base of a common shampoo bottle. He would be sore after this, but the orgasm that would come from being so full made it worth the pain. He placed the head of the dildo against his hole and pushed.

  Jess groaned out loud as his ass stretched around the dildo. He closed his eyes, reminding himself to breathe. There was pain, but not as much as other times he'd done this. His legs trembled as he pushed harder, then paused, again reminding himself not to hold his breath.

  "If you only knew how hot you look right now." Al's voice was filled with admiration. "You okay?"

  "Yeah." His words were hardly more than a gasp, coming out more a rush of air than a normal vocal sound. The head was just breaching him and waves of arousal and pain caused his mind to haze. He inhaled hard, then as he exhaled, he pushed the dildo deeper. "Ah, fuck!"

  "Look at that." Al's voice was loud as if he was closer to the microphone. "I've never seen anyone take something so large the way you do. How does it feel?"

  "Good." Jess spread his legs to see if it would help ease the stretch. He'd done this before and it did get easier each time, but the first few minutes were always hard. He had to focus on the pain, get lost in it, and turn it back into an odd kind of arousal. He'd heard of some men who enjoyed the pain so much they couldn't find pleasure without it. He wasn't that bad, but the pain sure did add to his arousal. The sting of it sent sparks up his cock and throughout his balls.

  "I'm just going to sit here and watch. You do what you need to do so you feel good. Just don't let yourself come yet. I'll let you know when you're allowed to come."

  "Can I touch myself?" Jess asked.

  "If you like."

  His cock was hard against his stomach. The way he was laying on his back had his knees bent, his feet braced under him. He'd practiced the position to make sure it worked well for the camera. It wasn't his favorite, but being on his knees hid his cock and face from the client's view. Most liked to see his face and his reactions, and they all wanted to see his cock.

  Jess moved the dildo, testing it against his hole, seeing how easily it would slide in and out of him. The excess lube made it easy, and he slowly started to fuck himself with the thick toy, moving it deeper inside him with each thrust. It wasn't long before he found a steady rhythm he liked and was able to use one hand on the dildo and one around his cock. He stroked himself, but it wasn't what he needed. The dildo was doing more for him. It pressed against that sweet spot deep inside him and sent lightning through his body.

  "Look at how your cock drips. You're so fucking tu
rned on." Al's voice was breathy and aroused. "I love watching you fuck—"

  "What the fuck are you doing?" Andy's voice came from the doorway.

  Jess's eyes flew open and he glanced over to find his friend staring at him in horror. Considering he had a huge, purple dildo stretching him wide, and was fucking himself like his life depended on it, he could hardly blame his best friend.

  Heat rose to his face as he tried to find his voice.

  "Jess, are you okay? Who is that?" Al asked.

  "Oh my God. Someone is watching you?" Andy gasped as he turned away and walked back out the door.

  "Go explain," Al told him.

  "No, I'm close, and oddly still aroused. I want to finish this. He can wait." For reasons he didn't understand, the knowledge that Andy had caught him doing this turned him on even more. It was the only secret he had from Andy, and now he didn't have to hide this job from his best friend, but even more, there was some perverted thrill at the fact that Andy had caught him fucking himself. He didn't even want to think what that meant.

  He used more force than normal as he thrust the dildo in and out of his ass. He moved his hips, riding the toy, aching from the width and stretch of it, but his cock was on fire. It was as if flames licked up and down his shaft and tiny explosions were taking place in his balls. Electricity raced up and down his spine as he gave in to the pleasure, holding back his release only because Al hadn't given him permission to come.

  He heard Al's breathing. It was harder and heavier than usual. Most times he was hardly aware of his arousal at all, but it was clear that Al was enjoying this. Maybe the unexpected intrusion had turned him on as well.

  "Come for me, Jess. Let me see how hard you come." Al's voice was shaky.

  "Yes." Jess gave in, twisting his fist under the head of his cock the way he loved. Once, twice, and one more tight fist down the shaft and his world exploded. Sparks of heat shot through him, his muscles tightened, his mouth opened, and a loud cry escaped him as he came. His ass clenched around the dildo, causing another jolt of pleasure. Seed spilled from him in spurts and it just kept coming. He'd never come this hard in his life. He arched off the bed, then fell back again, unable to control any of his actions because the release was so intense.