Pocket Change

by E. M. Leya

  "What are you doing?" Andy looked panicked.

  "Just changing into a nicer pair of underwear. It's how Al and I start every session. He'll have me get naked at some point, then either have me play with a toy or something while I jack off. It's up to you if you talk to him. I'm not sure what he has planned, but we'll just go with it." He hated how nervous Andy looked. Maybe this was a mistake. He thought that Andy could handle it. It was a lot of money to pass up.

  "I just watch?"

  "Yep, that's all he said you'd have to do. If he asks for more, that's up to you, but I don't think he'll ask. He really was turned on just knowing you saw me fucking myself. Once you get to know Al, I think you'll like him. He's a cool guy. Easy to talk to." Jess pushed down his whitey-tighties all too aware of Andy watching him. He stood naked for a moment, enjoying Andy's eyes taking him in. He didn't stay that way for long before he reached for a nice pair of burgundy underwear and slipped them up his legs. "He'll be calling any minute. Are you ready for this?"

  "No, but I'll get through it." Andy glanced at the computer. "What does he look like?"

  "I don't know. He's a client who doesn't turn on his camera. I've never seen him. I like to imagine him sexy. It helps me get aroused thinking some hot guy is watching me. Today, I won't have to think about him because I'll have you watching me. That will turn me on enough."

  "I'll turn you on?" Andy's eyes went wide.

  "Being watched will turn me on. Seeing you so close watching me will be a turn on. I like being watched by anyone." He wasn't going to freak Andy out and admit that he was aroused by the thought of Andy watching him. Of having Andy so close. He'd never let his mind consider Andy in a sexual way, but over the last week, he'd let his mind go there, and he'd had a lot of orgasms thinking about his friend in ways he never dared before.

  "Why didn't I know all this about you? That you liked being watched and that you like pain?"

  "How was I supposed to bring that up in normal conversation?" Jess climbed onto the bed, but didn't sit back. He'd have to lean in to turn on the camera once Al called. "When we talk about sex, we don't go into the details. I always held back cause I know you're not into what I am."

  "I never thought about the stuff you're into."

  "I know. You've been with women who are pretty vanilla. That's not a bad thing. I think that's how it is for most couples. I just find I like a bit more spice in my sex life. Most of my partners have been pretty tame. I don't admit to them everything I desire."

  "Which is why you like this? You can do things on camera that you can't do with a partner?"

  "Maybe. I haven't really thought too much about it."

  Andy nodded. "You'll let me know if I do something wrong?"

  "You're just going to watch. I can't see how you can do that wrong." The computer started ringing, alerting Jess that Al was calling. He leaned forward and hit answer on the app and smiled as the light on the camera came on. "Hi."

  "Hello. I wasn't sure what to expect tonight. I'm excited to see both of you here." Al's voice was cheerful.

  "Al, this is my best friend, Andy. Andy, this is my favorite client, Al," Jess introduced the two.

  "Nice to meet you." Andy's voice was shaky.

  "You too, Andy. Don't be nervous. I want us all to enjoy this." There was a pause, then Al said, "money has been sent."

  A second later, Jess's phone beeped with the incoming payment. "Thank you. We appreciate the payment. As you can tell, Andy's a bit nervous, but I've told him he can get up and leave if this gets too much. I can refund your money at any time. While we've been best friends for years, we've never done anything like this together."

  "You've seen each other naked?" Al asked.

  "Yes, in the locker room and while changing and stuff," Andy answered.

  "Good, then hopefully this won't be too rough for you. I know I'm asking a lot of you, but it really turns me on to see you there and know you'll be watching Jess along with me. To start, Jess, why don't you grab those nipple clamps and that small gold vibrator you have. Oh, and the lube."

  Jess leaned over to his nightstand drawer and started pulling things out.

  "Have you ever played with clamps before, Andy?"

  "No, never. I don't think I'd like them."

  "Yeah, I don't either on me, but I was just wondering if you were aware of how tight they clamp down. Would you mind letting Jess put one on your finger so you can feel how tight they will be against his nipples? I'd like you to know." Al sounded cautious, almost as if he knew that pushing Andy too far would cause him to run.

  "Sure." Andy held out his finger to Jess.

  "Don't pull away, the teeth on the clamp could tear your skin." Jess attached one of the clamps to Andy's finger.

  As the teeth bit into flesh, Andy hissed. Once on, he stared at his finger in horror. "You put those on your nipples?"

  "I like the pain." Jess released the clamp and smiled as Andy rubbed his fingers. "I told you that the pain brings me pleasure."

  "That's not normal." Andy shook his head.

  "Actually, it's not uncommon. I think Jess longs for even more pain than that, he's just never found anyone willing to give it to him. Someday, he'll meet someone who can give him what he needs," Al told them. "For now, Jess, will you please put those clamps on for me?"

  Jess did as instructed, breathing hard as each clamp pressed into his nipple. He closed his eyes and absorbed the pain.

  "Look at how hard that gets you. You haven't even touched your cock yet and you are aroused," Al pointed out.

  "Jesus." Andy gasped. "You're huge."

  "I thought you'd seen him before," Al said.

  "Never hard. I mean, yeah, when we were like fifteen, we jacked off together, but he's bigger now." Andy stared at the outline of Jess's cock through the underwear.

  Jess found having Andy look at him this way turned him on even more. He wanted to strip out of his underwear and show Andy all of him. He wanted him to see his heavy balls, and watch the precum drip. He resisted running his hand over his length, knowing he couldn't do anything until Al commanded him to.

  "He's got a beautiful body. Wait until you see him come." Al sounded so appreciative.

  Jess smiled. "Thanks."

  "How about you slide out of that underwear for me? Let me see how hot those clamps really have you," Al suggested.

  Like always, Jess made a show of sliding the underwear from his body. He was aware of Andy beside him, but he kept his eyes focused on the camera, reminding himself this was Al's show more than Andy's, though he wanted to watch Andy and see his reaction as his thick cock came into view.

  "So hard already. You usually don't get this hard until we start playing. You like having Andy there watching you, don't you?" Al asked.

  Jess wasn't going to lie. He nodded. "I like being watched. Having someone in the room with me is different than doing it on camera. I can hear his breathing, smell him, feel the bed shift when he moves." He glanced over at Andy, trying to read his reaction to everything.

  Andy stared at Jess's cock, then slowly lifted his gaze to meet Jess's. "You're so thick. Guys let you fuck them with that?"

  "Some, but I'm more the type that likes to get fucked. It's not very often that I am the one giving." Jess had told this to Andy before, but it was as if everything was suddenly making sense for him.

  "He's not as big as that dildo you caught him taking last week," Al said.

  "That was crazy. That thing was huge," Andy responded without hesitation.

  "It is huge, and he loves it." Al laughed.

  "I do," Jess agreed. "It's the pain thing again."

  "I don't understand that." Andy didn't sound or look uncomfortable, but more curious.

  "Tug on those clamps for me, Jess," Al instructed.

  Jess did as told, tugging on the chain that connected the clamps, causing his nipples to extend and pain to shoot through him. He closed his eyes, breathing hard through the electrical waves that coursed through him
.

  "Look at how his cock reacts, Andy. Look at the precum that's starting to drip from him. I've never known a cock to drip the way his does. I'm so jealous you're there to see it in person." Al's voice was low and filled with admiration.

  Jess watched Andy closely, worried he would freak out at some point, but he surprised him. He looked calm and curious, checking out Jess's cock just as he'd been told to do. Jess found himself surprised at how much he liked Andy watching him. He'd never let him think of Andy in a sexual way, but now, he wanted Andy to reach over and stroke him. He wanted Andy to be the one to tug on the chain and send pained pleasure through his body. Jess swallowed hard, forcing those thoughts to the back of his mind.

  "Grab that vibrator, Jess. Tease yourself with it a bit, but don't put it inside yet," Al instructed.

  Jess grabbed the slim, gold vibrator and turned it on. It was loud enough for everyone to hear as he spread his legs wider, eased back against the pillow, then started to run the vibrating tip over his balls and up and down his shaft.

  "Is that good?" Andy asked. "I figured you just fucked yourself. I never thought about using it the way you are. I know women like it, but didn't think men would."

  Al laughed. "Borrow one from him and take it home. You'll love the feeling. You hit that area right under your balls and it will blow your mind."

  "Seriously?" Andy watched intently.

  Jess nodded, feeling a bit breathless. "It's amazing. You really should try it sometime." He slid the vibrator lower and started playing with it around his hole.

  "Do you want to fuck yourself, Jess? Do you want that inside you?" Al asked.

  "Please." Jess fisted the base of his cock, but didn't stroke. He was so aroused and it was mostly because Andy was right beside him. He'd never had anyone who wasn't a lover watch him do anything before. He glanced over and was shocked to see Andy's shorts tented with arousal. Not wanting to embarrass him, Jess said nothing, but he was sure Al was aware of Andy being hard as well.

  "Let go of your cock. I didn't give you permission to touch it with your hand," Al commanded. "Grab the lube and get yourself ready."

  To his shock, Andy reached for the bottle of lube and handed it to Jess.

  "Thanks." Jess met Andy's gaze for a long moment, before looking away and turning his focus to opening the bottle and pouring lube over his fingers. He reached between his legs and slowly, teasingly rubbed the lube over his hole. He then slid two fingers inside himself, gasping in pleasure as he worked them in and out. He hardly needed much prep to take the tiny vibrator in his ass. It was slimmer than most of the cocks he'd taken in the past, but he made a show of stretching himself for Andy and Al to watch.

  "You shave everything?" Andy asked as if he'd just suddenly realized there was no hair.

  Jess smiled. "I can feel things better and Al can see everything. I like being smooth."

  "How do you… No, never mind. I don't need to know how." Andy shook his head. "How did I not know all this?"

  "You never asked." Jess sank a third finger in and twisted them. He lifted his hips, riding his fingers, enjoying this more than he should have. He could hear Al's breathing too, and that told him he was more turned on than usual since he seldom heard him breathe.

  "Grab that vibrator, Jess. Let us watch you fuck yourself with it," Al's voice was stern.

  Andy sat up straight and turned to face Jess as if he needed a better view.

  Jess hadn't expected Andy to be so curious. It turned him on that he was. He wondered what the conversation after this would be like. Was Andy interested in playing with toys on his own now? Had this opened up a new world of sexual pleasure for Andy to try? Precum dripped down his hip as he reached for the vibrator and rubbed lube over it. He was more than ready to take it, and he slid the tip against his hole and slowly eased it inside.

  "Shit, that doesn't hurt?" Andy asked.

  "Not a bit. I've done it often enough." Jess started to fuck himself with the vibrator. He had it turned up all the way and it sent shocks like fire straight to his prostate. His cock jerked and swelled without him even touching it.

  Andy's breathing was coming harder, and the tent in his shorts grew bigger. Part of Jess wanted to reach over and touch it, but he was sure he'd freak Andy out if he did. He forced himself to try and forget Andy was so close and turned his full attention to giving Al a show. He couldn't forget him. He was the one paying for this.

  "If you're comfortable doing it, Andy, reach over every so often and tug on those nipple clamps for me. Just grab the chain and give it a small tug," Al suggested.

  Andy did as he was told, tugging on the chain gently, then releasing it as Jess cried out in pleasure.

  "Sorry, I didn't mean to hurt you," Andy said.

  "You didn't. That was pleasure." Jess took a deep breath as he continued to fuck himself. "Do it again. A little harder. Hold it for a second if you want."

  "You're insane," Andy said, but even as the words left his mouth, he reached over and grabbed the chain, pulling it a bit harder this time and holding it, watching as Jess's nipples stretched a little from his chest.

  "Oh, fuck!" Jess's head arched back. "Please, let me touch my cock."

  "Not yet." Al's voice was firm.

  Andy pressed down on the bulge in his shorts as if he were trying to hide it.

  "Tug on it again, Andy," Al commanded. "Make him suffer. Watch how his cock reacts to the pain."

  Andy tugged on the clamps again, and just like Al had said, Jess's cock jerked and a bit of precum wept from the head.

  "I'd love to see how much pain you can really take." Al's voice was filled with arousal. "Stop fucking yourself and run that vibrator over your balls again."

  Jess groaned as he slid the vibrator from his ass and moved it back to the base of his balls. He was so close to coming. He only needed permission. He wanted to watch Andy's face as he came, but he was sure he wouldn't be able to keep his eyes open when he finally was allowed to find his release. God, this was too much. He could feel Andy move on the bed, hear his breathing, and was stunned at how interested Andy was in what he was doing. He'd thought Andy would pretty much sit there and ignore, but he was watching, leaning in, and asking questions. And he was aroused, which stunned Jess. He lifted his hips, wishing he could fuck himself some again. This wasn't enough. He needed more.

  "So fucking hot. You were made for sex, Jess. I love how alive your body becomes. Does it turn you on more knowing your best friend is watching? Do you like having someone else in the room with you?"

  "Yes." The words came out on a gasp as the vibrator hit a sensitive spot.

  "Do you want to let Andy watch you come?"

  "Yes, please." Jess wanted nothing more than to wrap his fist around his cock and come hard.

  "Let's let him decide when you can come. Go ahead and touch your cock, but you aren't allowed to come until Andy tugs on that chain again. He can make you sit there and wait as long as he wants to, but the moment he pulls that chain, you have my permission to come. Is that okay with you, Andy?" Al asked.

  Andy cleared his throat, his hand still pressed to his crotch as if holding his arousal down. "Yes."

  "Good." Al sounded pleased. "It's all up to you, Andy."

  Jess kept the vibrator against his balls, but used his other hand to start jerking off. His hands were still smeared with lube and it made the glide of his fist easy against his thick arousal. His stomach tensed, his balls pulled tight, but he managed to hold off his orgasm, determined to give both men watching him exactly what they wanted.

  "How long can he last?" Andy asked.

  "He's never come without permission," Al told Andy. "I've watched him teeter on the edge for about thirty minutes before. Just when I'd think he couldn't handle any more, he somehow found a way to hold back. He's amazing. It takes a special kind of man to have that kind of control," Al explained. "If you ever feel the urge, watch edging porn. Someday, I'd love to see someone edge Jess. I want to know how much he can ta
ke."

  "I've seen edging videos, but women edging men. They were hot, but not something I'd want done to me. I don't have that kind of control," Andy told them.

  "Most don't have the control Jess does. He's trained himself well. He was made for this stuff. To give and receive pleasure. I've never seen a sexier man," Al said softly. "Just look at how hard he works that cock. Look at how aroused he is. Yet, he is in complete control. It's amazing to watch. And the second you tug on that chain, he'll come. There won't be any hesitation. It will be on-demand. It's perfection to watch."

  Jess listened to them, caught in the haze of arousal, focused so hard on staying in control that he didn't dare comment on what they were saying. He longed for Andy to tug on the clamps, to give him that bite of pain that would throw him over the edge. He needed this release. Needed to have Al and Andy watch him.

  Without warning, Andy reached over and pulled the chain, harder than he had before. Pain shot through him, sending sparks of agony through him and they all seemed to settle in his balls. Fire lit inside him, licking its way up his cock, and before he could do more than cry out, he came, hot streams of come shooting from his dick, covering his hand and his body as he arched into the pleasure, his muscles contracting, his world going black for a few seconds before he collapsed.

  "Jesus, that was crazy. Does he always come that hard?" Andy asked.

  "Never. He comes hard, but I've never seen him like that. He must like having you here with us," Al told him.

  Jess smiled weakly, but couldn't speak.

  "Would you consider joining us next Friday?" Al asked Andy.

  There was a moment of silence before Andy spoke. "Um, doing the same thing?"

  "Yes, unless you are willing to help me with something. I know you aren't gay, but I'd like to see what different kinds of pain do for Jess. How he handles it. I'd pay you both the same amount." Al's voice was soft, almost unsure.