by E. M. Leya
When it finally faded, he lay spent against the pillows, sweat covering his body, and his breathing so heavy that he wondered for a moment if he would ever recover.
"That was the hottest thing I've ever seen in my life," Al said.
Jess giggled. Fucking giggled. He never giggled. It was a testament to how spent he was. "I can't move."
"I bet. I don't think I've ever seen anyone come so hard." Al laughed. "You liked being caught, didn't you?"
Jess opened his eyes and glanced at the camera. "Was it obvious?"
"To me, but I make a habit out of knowing your reactions. I expected you to be horrified and stop, but instead, you just kept going, harder than before. Your cock gushed precum when he slammed the door shut."
"I'm never going to live this down." Jess laughed, not actually worried about Andy, but unsure of how his best friend would react.
"Is this going to be a problem for you?" Al asked.
Jess sat up and eased the dildo from his ass. He made sure to do it slowly so Al could enjoy it. He then kept his legs wide so Al could see his gaping hole as he set the dildo aside. "No, I don't think so. It was Andy. He didn't know about me doing this video chat stuff, but I think he'll understand. I think once I explain…" Jess shrugged.
"It won't ruin the friendship?"
"No, we're too close for that. He knows I have a kinky side. I just can't tell him how much I liked getting caught by him." Jess wiped sweat from his forehead. "Is that weird? I never thought I'd get turned on by something like that, but it was kind of hot thinking about what he saw when he walked in."
Al was silent for a moment, then said, "I liked it too. I liked knowing I wasn't the only one watching you. I wasn't the only one amazed at what you were doing."
"I'm not sure he was amazed. He looked horrified." Jess licked cum from his fingers, again making sure to do it so Al could see.
"I have a question, but if it goes too far… If it's something you don't want to do, just tell me."
"What?" Jess focused on the camera, curious what Al could ask. They'd done almost everything on camera together they could. Nothing made Al sound nervous.
"Does Andy need money?" Al asked softly.
"Yeah, of course." Then Jess's eyes went wide. "Oh, no. I don't think he'd do this for you. He's not gay. He wouldn't get naked for another man. Some chic, maybe, but not a man."
"I'm not asking for him to get naked. I simply enjoyed the thought of another man watching you. Do you think he'd sit on the bed beside you, fully clothed, and let me watch him watch you?"
Jess's heart slammed in his chest. "Watch me?"
"Yeah. Maybe I'm a pervert or have some strange fetish, but I want to watch you play with yourself while your best friend watches. The fact he's straight makes it even hotter in my mind."
"I don't know." Jess shook his head. "I mean, Andy's up for a good time, but with me? With us? I just don't know that he'd do it. I'm willing, but he probably won't be."
"I'll pay you each five hundred dollars for an hour of it. Andy can stay dressed the whole time and doesn't have to touch you. He only has to watch you." Al sounded as if he was excited, his words coming out breathy.
"Just watch?"
"Yep. If you want, ask him to join us next Friday night. If this isn't something you want, then we'll just keep going as we have, just you and me." Al sounded as if he set something heavy down. "Go and make sure Andy is okay. I'll call on Friday at our normal time. You were extremely hot tonight, Jess. The hottest I've ever seen you." With that, Al disconnected the video call and the green light faded out.
Jess closed his eyes, still weak from his orgasm as he thought about what Al had suggested. It was a lot of money. Money they both needed desperately, but he just wasn't sure if Andy would do it. They talked about sex all the time, but this was something different. Jess sighed. Before he suggested anything, he needed to explain what Andy had walked in on. First, he needed to clean up, then he'd see if Andy had fled the house or was waiting in the living room for him to come out and explain.
CHAPTER FOUR
Andy sat staring at the T.V. but he didn't even notice what was on it. He couldn't get the image of Jess out of his mind. He'd never seen anything like it. Sure, he'd seen Jess naked a million times over the years when they'd changed clothes or stayed overnight at each other's house. Hell, they'd even jacked off together to porn a few times when they'd been in their teens, but this? This was something he'd never expected to see.
He ran his fingers through his hair, remembering the thick dildo that had spread Jess's ass apart. Why would someone do that? He'd had a woman finger his ass once and it hurt like hell. The thing Jess had up his ass had to be as big as a fist. And who the hell was the other guy? Why was Jess doing video chat of him fucking himself? If he had a boyfriend, he'd have told him. They didn't keep secrets.
His mind went back to the way Jess had avoided his questions when they'd gone out to dinner the week before. Could he be hiding someone? If so, why?
Maybe he should go. Any conversation now was going to be awkward. Jess didn't owe him any explanations. He probably should have knocked before opening the door, but he'd never had to knock before. He didn't do anything they both hadn't been doing for years. They both gave each other full access to each other's apartments. Hell, they had keys to each other's places just in case they needed them.
"Fuck." He slumped back against the couch, unsure what to do. What the hell was he supposed to say? Nice ass? What the fuck? Didn't that hurt?
It was no surprise that Jess was kinky. He knew he had toys. Hell, he'd been there when he'd bought some of them, but he had no clue he used things as big as the one he'd seen, or that he would do it while chatting with someone online. What the hell was Jess into?
A soft sound had him looking up to find Jess walking into the living room. His hair was wet as if he'd just showered and he wore an old pair of sweats. His chest was bare, but that was common when they'd hang out. He stared at Jess, unsure what to say.
"Sorry you had to see that." Jess's cheeks pinkened, which was strange because truly little embarrassed Jess.
"My fault. I didn't knock. I got here early and thought you might be sleeping. I was going to tell you to get your ass up." Andy couldn't hold eye contact with Jess. Not after what he'd seen.
"I mentioned I had a meeting." Jess sat down and reached for a beer out of the case Andy had yet to put in the fridge.
"Yeah, you said some life skill class or something?" Andy raised a brow. "I'm not sure I want to know what kind of skills you are learning on there."
Jess released a small laugh. "Yeah, I can imagine. Actually, no, I can't. I don't have a clue what you must be thinking right now." He opened the beer and took a long drink, then set it down on the coffee table. "I lied about the class."
"Obviously. And that's okay, but what I don't understand is why you'd keep the fact you had a boyfriend quiet. You've never hidden that from me." Andy glanced over at Jess, then looked back down at his shoes, still unable to get the image of Jess's filled ass from his mind.
Jess sighed and leaned back. "It wasn't a boyfriend. It was a client."
Andy quickly turned to face Jess. "What? A client? What the fuck, Jess?"
"I know, but I needed the money. It's easy money. I'm going to jack off every day anyway, I might as well let people pay me for watching me do it."
"Um, that was a lot more than jacking off."
"Okay, so maybe I do a bit more, but nothing I don't want to. I get off and I get paid. That's all that should matter, right?"
Andy ran his fingers through his hair as he tried to understand. "I don't know. How do you know you can trust these guys? It is guys, right? You aren't doing this for women?"
"No, but I would if they paid. I've just never had a woman answer any of my ads." Jess shrugged.
"So, let me get this straight. You place ads offering to let people watch you shove some impossibly big cock up your ass?" He shivered at the thought.
There would be no way any sane person would do that.
Jess blushed again. "No." He sat up again, bracing his arms on his legs. "Not usually at least. It was different tonight than usual. I do things with Al I won't do with other customers."
"Because there's something more between you?" Andy was so confused.
"No, it's not like that with him. Well, in a way. Most of the men I perform for are just customers. It's just sex, but I've formed a friendship with Al. We talk. That's something I don't do with any of the others. With him, it's just different, but we aren't involved in any romantic way. I don't feel anything for him other than friendship."
"How many others are there?" He was torn between wanting to know everything and fearing what he might find out.
"It depends. I have a few steady customers I meet with once a week, then I might throw in a few others if I have the time. Not very many. Just enough to help pay the bills."
"You make a lot?"
"A hundred dollars an hour."
Andy's eyes widened. "Seriously? For masturbating on camera or do you always do shit like I walked in on?"
"Most of the time it's a little dirty talk and me jacking off. Sometimes I'll use a vibrator or dildo but seldom do I do what you saw tonight, and if I do, it's only with the one client," Jess explained.
"Customer or client, you've said both."
"Does it matter? Same thing, isn't it?"
"How did you get into this?" There was so much Andy didn't understand.
"By accident really. I was just chatting on this app that a lot of gay men use to find dates and shit. Some guy asked me if I'd jack off for him and offered to pay to watch me. I really needed the money, so I did it. It was after that I found out that there is money in doing this. I put an ad up on a message board and by the next morning, I had thirty offers to pay me for different things. I was picky, but decided to give it a try. I've been doing it about a year now."
"Holy shit." Andy shook his head. "Why didn't you tell me?"
Jess looked down at his lap and shrugged. "I didn't know how. I didn't know what your reaction would be."
"It would probably be better if you'd told me than for me to walk in and see…" He shook his head. "How the hell do you do that? It had to hurt."
Jess reached for his beer again and gave him a sideways glance. "You really want to know?"
"I don't know. I can't get what I saw out of my mind. Why would you do that to yourself?" He couldn't imagine willingly putting anything up his ass, but he was still fascinated with what he'd seen. He wanted to know more.
"I enjoy it. Yeah, it hurts, and it took time to be able to do it. I had to stretch myself with other toys first, but I get off on the pain and fullness. I have my best orgasms when I'm using it. It's hard to explain, but there is something about the mix of pleasure and pain that makes things so intense."
"You sound like this submissive woman I heard talking on some video. She was talking about something called subspace and how the pain added to her satisfaction. I didn't understand it all. She was into being whipped and shit. You're not into that, are you?"
Jess shrugged again. "I've never done it, but the idea of it turns me on. I understand how the pain could be arousing. How it could add something to the sex. I've never been with anyone willing to do that stuff, so I don't know. I have played with things like nipple clamps and stuff, and I loved those."
Andy shook his head, but the truth was, this all aroused him. Not that he'd tell Jess that.
"I get it's not for everyone. That's probably why I've never brought it up with you. I know you're okay with me being gay, and we talk about the simple things, but I thought all of this might be too much," Jess admitted.
"It's not too much to talk about, but I really didn't need to walk in and see that." Andy laughed. "I'm sorry. I didn't even think about knocking. I hope I didn't lose you any money ruining whatever you had going on with that guy."
Jess bit his lip.
"What? He refused to pay you?"
"No, actually, he sent a big tip after. He said the idea of someone else seeing me like that turned him on. He liked me getting caught that way."
"That's creepy."
"Not really. I understand him because… I'm not saying this trying to freak you out, but it turned me on too. I knew you were horrified, but it turned me on having someone else see me that way, even if it was you."
Andy didn't know how to respond. What was he supposed to say to that? He wasn't about to admit there was a part of him that wanted to stay and watch, if for no other reason than to believe what he was seeing. "Well, I'm glad I didn't lose you any money."
"You actually could help me make more money because of it." Jess eyed him warily.
"How? You want me to walk in on you like that more so other customers will tip better?" He laughed, but it really wasn't funny. He'd be ultra-careful opening Jess's bedroom door from here on out.
"No. Al was so turned on knowing you saw me, he asked if you might sit in the room and watch me do stuff."
"He wants me to join in?" Andy held up his hands. "Sorry, I'm not into that video shit."
"No, I mean, yes, you'd be on camera with me, but you'd be clothed and just sitting there watching while I did stuff. It's the idea of having you watch me that turns him on. He offered us each five hundred dollars to do that."
Andy's mouth fell open. "Five hundred?"
"Yeah. I get the feeling the guy is rich, but we've never talked about it. He pays me before each session, then sends a tip after. I told him I doubted you would. He knows you're not gay, but I promised him I'd ask." Jess tipped back his beer and finished it before reaching for another.
"Fuck, this is insane."
"I know. I'll tell him I asked and you refused."
"No, what's insane is I'm considering it. I need money." Andy stood and started pacing in front of the T.V., unable to believe he was seriously considering this. "I just have to watch? I don't have to touch you or get naked myself?"
"Yeah, I guess just sit on the bed beside me while I get myself off. You'd have to watch. You couldn't turn away or anything." Jess shook his head. "Just forget it. It's a crazy idea."
Andy knew how tight money was for Jess. Five hundred dollars could help a lot right now. Hell, it would help both of them. He turned to face Jess. "It's not like I haven't seen you naked before, but this is a bit different."
"Yeah." Jess looked up at him. "A lot different."
"Does it freak you out?"
"Not really as much as it probably should. I'm used to doing this for men I don't know. Doing it in front of you should be easier than that, right? Fuck, I don't know. It's weird, but…"
Andy sighed. He knew Jess was thinking about the money. Hell, he was thinking about the money. "But it might be worth it?" Andy stared at his best friend, wondering if they dare do this. "Can we handle it?"
"You mean our friendship?" Jess asked.
"Yeah, I don't want to do this if it's going to change things between us. I don't want things to get weird."
"Do you think they might?"
"I don't know. I'd like to say no, but can you honestly expect me to watch you shove a huge cock up your ass like that and not see you differently? I'm not judging, honestly, I'm not, but…" But what? The whole thing was fucked up, but refusing to do it was insane. They both needed that money. It would be one hour out of their friendship. Surely, they could recover from that. He met Jess's gaze. "Let's do it."
"You're sure?" Jess stared back.
"Yeah, we both need that money. I can handle it. I saw the worst of it today, right? Call or text him or whatever and tell him I'll do it."
"He said he'd get with me Friday night like always and if you were there, he'd send more money, if not, we'd do a normal session like always." Jess set his beer down. "You're really okay with this?"
"It'll be like watching porn. I've sat through gay porn with you before, haven't I? I'll just try to forget you're my best friend. Once it's over, we can
get drunk and forget it ever happened." At least he hoped they could forget.
"You're the best. Thank you for this." Jess looked relieved. "I'm sorry I didn't tell you about all of this before. I promise, from here on, no more secrets."
Andy moved back to the couch and took his beer off the table. "Just be safe, okay. Don't take this too far."
"I promise." Jess smiled. "Now hand me that pizza box. I'm starving."
Andy passed the box to Jess, hoping that he could make it through the next week without freaking out and changing his mind.
CHAPTER FIVE
Jess was nervous as he set the laptop on the bed and positioned it correctly. "Come sit beside me for a second. I need to make sure to get both of us in the shot." He glanced over at Andy, who was leaning against the closed bedroom door. His face was pale as he stared directly at the bed.
They'd hardly talked all week, but Jess was sure it was all that Andy had thought about. It had been all he could think about. While he was excited for the extra money, it was going to be strange to have someone in the room with him for a change. He had no idea what Al might ask him to do. He prayed it wasn't something crazy that might cause Andy to get up and leave.
"This is insane." Andy slowly made his way to the bed and sat down on the far edge.
"I know, but it will be over in an hour and we'll have our money." Jess messed with the camera. "You're going to have to get closer. I can't get us both in the shot." He'd put the laptop on a small table at the foot of the bed to increase the area the camera picked up, but it was still limited.
Andy kicked off his shoes and moved farther on the bed. He relaxed back against the pillows. "This work?"
"Yep, that's perfect. He'll be able to see us both." Jess met Andy's eyes. "We've shared a bed a million times in the past. I know this is different, but I couldn't do this with anyone but you. You can stay just like you are. You don't have to get closer and you don't have to touch me. Just watch. If you can't handle something, speak up. We aren't going to make you stay if you honestly can't." Jess started to undress.
