Craigslist

Published on Oct 19, 2008

Gay

Craigslist 9

WARNING

This story details explicit gay sex between men, teens and boys. If you find this kind of thing distasteful, or if you are underage where ever you live, then stop reading this now, and delete this file. The story is completely fictional, the author does not condone or encourage any of the acts contained herein.

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Chapter 9

I call Gary after talking with Jason and accept his invitation to Santa Cruz. Gary has a beach-front condo there that he bought years ago for cheap, and is worth probably a million now. Right across the street from the beach. Jason takes his Speedo, and I take a pair of shorts and a t-shirt. It's a beautiful day. We agree to car-pool, and arrive at Gary and Nathan's at about 9am. I ring the bell, and Nathan appears at the door a few seconds later, naked. He is a really beautiful boy, but not as beautiful as Jason. I've got the winner in this contest. He hugs us both, and runs to get Gary, and we get under way quickly, Nathan dressing quickly in short shorts, a t-shirt and sandals. I giggle. He looks so gay. We head out. Nathan and Jason are in the back, chattering away, and Gary and I are in the front.

This drive scares me a bit. Highway 880 is not my favorite. Too windy. I'm not fond of driving at the best of times. But Gary loves it. I'm a little concerned about Jason, because he tends to get car-sick on drives like this, but he appears to be too engrossed with Nathan to care. Nathan drew a red 25 this morning, and Gary apparently had him so close to cumming, through fucking and stroking him, that he was nearly certain that a red ass was imminent. Somehow Nathan made it, though. Either happily or unhappily, he managed not to cum. This truly is an insidious game, and one Gary can't lose. If Nathan cums, he's beaten. If he doesn't cum, he has blue-balls, as he does now. You can tell by the level of energy he displays that he's really having trouble with this, and this is only day five of 182. Jason confirms this later in the day, telling me that Nathan is seriously frustrated and close to tears for much of the trip. Celibacy for this boy truly is torture.

We don't bother stopping at the condo, but instead go directly to the beach. The temperature is somewhere between 75 and 80 degrees, perfect. Sunny. And the beach is, surprisingly, sparsely occupied, but it's still early. Grabbing our stuff, including a huge blanket, we stake out our spot, the boys looking for somewhere to change. Gary winks at me. "Do it here," he says.

Jason looks to me, clearly very reticent. I nod. "Do it here."

Jason looks around. Nathan looks around. Not too many others. I've never seen clothes fly off faster than this. They're naked and in their respective Speedos in nearly and instant. And, my god do they look good, although, again, Jason's body type, short, compact, attracts me more than Nathan's. I know that Gary's just the opposite, and that's a good thing. But I just can't keep my eyes off Jason. He is absolutely beautiful as he and Nathan frolic, running in and out of the ocean.

Speedos are amazing things. They show nearly everything, but withhold just enough, leave just enough to the imagination, to be really erotic. Seeing Jason and Nathan running around on the sand in next to nothing gets me hard, makes me want to touch him, actually makes me want to touch them both.

I grin at Gary. "Have you ever done a four-way?"

He frowns. "I don't do group sex very well. I get a bit inhibited."

I look at him, surprised, amused.

"Yeah, I know. You wouldn't expect it of me. I wouldn't expect it of me either." He grins. "Can't get it up. I enjoy watching it, though."

It's almost an invitation. "Would you mind if Jason, Nathan and I went at it?"

He pauses, thoughtfully. "Actually, I think that'd be really hot. But Nathan's not allowed to cum today."

"Well, you can either give him a special dispensation, or we can bring him right to the edge, and stop."

This produces a belly-laugh. "While I might trust you to pull that off, Jason has neither the skill nor the inclination to achieve that level of...torture. And Nathan is pretty...keyed up right now." He chuckles. "No, it'd have to be a dispensation, as you say. He's been really sweet the last few days, I have to admit. He probably deserves some slack." He pauses, and then grins. "Yeah, why not? We can do it in the condo. Mind if I film it?"

"Long as you don't put it out on YouTube. That'd sure as hell dry up my career." I smile.

"No worries. I just may want to watch it again. Good jerk-off material..."

"No problem," I grin.

Jason and Nathan are in the water, splashing each other happily, laughing and giggling, screaming at each other in Cantonese, their bronze skin almost sparkling in the sun. This will be a blast. It makes my dick hard just thinking about it, a fact that is not lost on Gary.

After another hour or so, we manage to get their attention and reel them in. "Let's head up to the condo, guys, and get some lunch," says Gary.

The beach is now crowded, and there's still nowhere to change. The boys look around, confused. "I wouldn't worry about it," I say. "We're going to be `home' in about three minutes." I giggle.

They both look a little worried, but Gary and I start to walk toward the condo, and the boys follow. When we get there, Gary unlocks the door and the boys file in, Nathan walking to the bathroom to get dressed, and Jason following. "No clothes, guys," Gary commands, and I nod at Jason. They stare at us for a few seconds, look at each other, a bit embarrassed, and then both strip. They are both perfectly hairless. I shaved Jason this morning, one of my favorite morning rituals, and Nathan is also stubble-free. He also has a slightly pink ass. They take their Speedos to the laundry room and hang them from the clothes line to dry, and then go to the kitchen to make a simple lunch of tuna-salad sandwiches. Like me, Gary likes his food spicy, and so the tuna salad is laced with Jalapenos and...curry power, I think. Just delicious.

As we eat, I broach the subject of our impending three-way. "As we were sitting on the beach, working on our tans," I begin, and Jason snickers. "What are you laughing at?"

He snickers again, and Nathan snorts. "You guys are pretty pasty white. I don't think that work worked."

Gary snaghs.

"You are getting so punished tomorrow," I laugh. He grins.

"As we were sitting on the beach watching the two of you frolic," I begin again, "I found myself...umm...getting hard."

The boys look surprised. Not at my reported condition, I think, but at the fact that I'd admit this.

"I asked Gary if he'd consider a four-way. He said that he wasn't into that, but he'd like to watch." I smile, coyly.

Nathan looks confused. Jason looks worried. I've baffled everyone, which I think is great.

"So, I suggested a three-way, and he agreed."

You can see the very mixed emotions of both the boys. Nathan is so sex-deprived he can almost not stand it, but he's also very shy. I've sensed that he's attracted to me in the past, but he doesn't want to show that, doesn't want Gary to know. Jason is jealous and hurt. He's basically a potato queen, attracted only to Caucasians. He doesn't want to share me -- or himself -- with Nathan. He's sad, and a little angry. But he wants desperately to submit. It's my job to sell this.

"Jason," I say, moving into him and kissing him. "I love you so. You're the most beautiful thing I've ever seen. And, you're smart, funny. I don't know how I could love anyone more. And, Nathan, you're just flat out cute, and suffering from a perpetual raging hardon. You're very sweet, though not Jason, and I've convinced Gary to let you cum today if you'd like to. You've apparently been a good boy recently." I giggle.

Nathan stares at Gary, who nods. Nathan smiles, and moves to Gary, and, sitting on his lap, hugs him.

"But...the way you have to get off is with us."

He smiles at Gary, and Gary nods again.

"You won't join us...please?"

Gary isn't as tough as he'd like you to believe. Gazing at Nathan, the love of his life, you can see his heart begin to melt. "I'm not very good at these kinds of things."

"Please?"

A half-smile appears on his face, but also concern. He's worried about performance, and Nathan knows it.

"It's okay, sweetie," Nathan says. "I will not enjoy this without you." He leans forward, and kisses him, and it becomes one long, passionate kiss. Jason smiles at me and giggles, and I smile back. Eventually, someone breaks the kiss and Nathan backs off.

"Okay," Gary agrees. "After lunch."

Nathan hugs him tight, giggling. Finally he releases him, letting him finish his sandwich.

After lunch, we take a short nap, 45 minutes at most, all in Gary's king size bed, all, now, naked. It's an apt prelude to sex, because, as we wake up, we find ourselves all literally intertwined. Gary and I are at either end of the bed, with Nathan between us. Jason is lying across all of us. How he came to be that way, I have no idea. And he's the last to wake up, finding himself lying across our three bodies. For a moment, you can tell he doesn't know where he is, or how he got there. Then he looks embarrassed. "Sorry," he says. Then I tickle him, and he starts to giggle madly while Nathan holds him in place. Finally, I stop tickling, and start to kiss him, a long sensual kiss. After a minute or two, I reach for his cock, and find Nathan's hand already there. Jason is rock hard. Breaking the kiss I look over at Nathan, who smiles. "Guess that worked," he says, giggling.

Nathan's face is an inch from mine, so I move in and start kissing him, and he returns that kiss in spades as Jason starts sucking my dick. Breaking the kiss, Nathan turns to Gary, and they start to make out, Nathan rubbing his dick against Gary's leg. Soon, Gary is jerking him off until Nathan breaks away. "No," he says. "I know this is a gift. I know I might not pick that green marble for months. I don't want to cum like that."

Gary looks surprised, and even Nathan looks up from his ministrations on my cock. Both Gary and I laugh, and Nathan sulks.

"I'm sorry, baby," Gary coos in his ear. "How do you want to cum?"

Nathan looks pensive, and then smiles broadly. This should be good. "I want you to fuck me while Tim sucks me, and Jason kisses me." We all begin to laugh, to poor Nathan's chagrin. Gary looks at me to see if I'm game, and I wink, playfully. He looks at Jason, who smiles and shrugs. And then we begin the acrobatics this achievement will require. Gary pushes Nathan onto his knees, while I position myself on my back under his cock, and Jason positions himself on his back facing Nathan. Good thing Gary has a king-size bed. Taking a tube of lotion, Gary lubes his dick and smears a generous amount on Nathan's hole. He enters him in one slow thrust as I begin sucking him, and Jason begins kissing him. Watching the kiss from the corner of my eye is almost enough to make me cum, but I hold out, waiting for Nathan's response. This is his fantasy, after all. Jason is using his left hand to hold Nathan's head in place, caressing the back of his neck, kissing non-stop, their tongues intertwined. (Have I mentioned that Jason is a really good kisser?) His right hand, I find, is kneading my cock, jerking me off, while Gary strokes Jason even as he pumps in and out of Nathan. I, in turn, am playing with Gary's balls and asshole. We are like a giant octopus, so wrapped around each other that we may never disengage. We do this for probably ten minutes before Nathan groans and begins pumping a load into my mouth, still kissing Jason. This sends Gary over the edge. Jason has been working my cock non-stop, and I begin to cum, watching all this, and Jason too suddenly erupts from Gary's fine handiwork. As our collective orgasm subsides, we slump, exhausted, and Jason begins to giggle, and then Nathan begins to giggle, and then we all begin to laugh outright. None of us, I think, have ever done anything like this. Just the lowering of our `shields,' overcoming all those inhibitions, has made us giddy.

Nathan: "Umm...that was nice."

We all begin to laugh again for probably another five minutes, until our bellies ache. What a fucking understatement: "Umm...that was nice."

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We decide not to go back tonight, but to stay in Gary's condo. He only has one bedroom, and one bed, but it's comfortable enough, and it's not like we have anything to hide -- not after this afternoon. We go to a steak restaurant that Gary knows. Personally, I've never been able to find anything good to eat in Santa Cruz, but this isn't bad, although I'm not used to eating this much meat. Gary and Nathan each order a filet, and Jason and I go for a single order of prime rib, which we share, and a bowl of soup, which we also share. And then we wander down Ocean Avenue, the main drag, stopping at the book stores, and a couple of curio shops. Heading back to the condo, we decide to make our way back to the beach to watch the sun set, and spend half-an-hour sitting on a low retaining wall, necking, drawing the wrath of one passerby, who calls us faggots. There are assholes everywhere, I guess.

Holding Jason in the moonlight is so nice, so comfortable. He fits in my arms so well.

Finally, we amble back to the condo, have one last glass of wine, and turn in. The sleeping arrangements are cramped -- and delightful. Once again, we're completely wrapped around each other. Gary is at one end of the bed, and Nathan is spooned up against him, his arms wrapped around him. Jason is spooned up against Nathan, and I'm spooned up against Jason, holding him tightly. I guess we never move, never change directions, because this is how we find ourselves the next morning, except Jason has flipped, and we're now face to face. When I awake, his eyes are already open. I move in and kiss him, and he hugs me, attaches himself to me, his head draped over my shoulder. "I love you," he whispers.

"I love you, too," I reply, tightening my hug.

Gary and Nathan begin to stir, and soon we're all in the shower, washing down.

Gary has brought the bowl of marbles, and once we get out of the shower and towel off, Nathan gets to choose from the seven in the bowl. He chose the...

...fucking green marble.

He stands, dumbfounded, staring at the marble, and then at Gary, who is smiling, and then at us. We're also smiling. The brass ring. He can't believe it. He stands staring at the green marble, his dick at attention.

Gary starts to laugh at his expression, his amazement, his erection. "You thought last night was going to be the last time you'd cum in the next six months, didn't you."

Nathan looks at him, angry and amused at the same time: "Yeah."

Gary continues to laugh. "Well, this might be." He looks to us. "I'm sorry, guys, but you're captives right now. I had no idea this would happen, but Nathan's need to get off takes precedence now. He's only got twenty-four hours."

"Well, I'm sorry, Nathan, but I have an important meeting." I look absolutely serious.

He suddenly goes sad on us.

Petting his hair, stroking the back of his neck, "No. I'm kidding. We're fine. For another day. Right, Jason?"

He smiles. "For another day. You need to be in Sunnyvale tomorrow at 2pm. You'll need to look nice."

I smile at him, and so does Gary. And so does Nathan. "I always look nice."

Jason giggles.

"So what's it going to be, Nathan? However and as often as you want?"

He looks guiltily at Jason and me, hangs his head. "Could you guys stay out here? I'd like to go to the bedroom with just Gary. Maybe watch TV for a while, or maybe a DVD?" Jason and I giggle, and put in the old Ziffirelli "Romeo & Juliet," which always makes me cry. Just as Romeo dies, Gary calls us into the bedroom.

"Nathan is apparently done with me," he says, playfully, and Nathan cuffs him on the arm, eliciting a snaugh from Gary. "What he'd like now is to recreate last night. Except, he'd like Jason to suck his dick, and Tim to kiss him." He starts to laugh again, and Nathan cuffs him again, with a playful smile on his face. Jason and I look at each other, giggle, and nod.

We get into position, and Gary drives into him. Jason starts sucking, and I start kissing -- in earnest. Nathan is also a very good kisser, I find, and is jerking me off at an alarming rate.

Recreating last night is going to be tough. Last night we all came at relatively the same time. Today, though, at this moment, Gary and Nathan have been fucking for the last two hours, while Jason and I haven't been sexually active since last night. Holding out until Nathan cums is going to be tough, I think, especially as good as Nathan is with his hands. Jason, too, is having trouble, moaning non-stop as I stroke him with my right hand. After about fifteen minutes, during which Jason and I have done our best to hold out, Jason gives a mighty groan, and fills my hand with his spunk, which causes me to lose it and I fill Nathan's hand. Surprisingly, this sends Nathan over the edge, and as his orgasm subsides, Gary starts his, firing into Nathan. Dominos. After a few minutes of post-orgasmic panting, we disengage.

Gary and Nathan are spent. They can barely make it to the shower to clean up. I use a tissue to wipe my hands, and then Jason and I lounge on the bed, still naked, waiting for the shower.

Lying on our backs, we whisper to each other, giggling about the four-way. There's a pause in the conversation, and then Jason is on top of me, belly to belly. We begin to kiss, and this kiss goes on for probably ten minutes as Jason rubs his now engorged cock between my legs, hitting me in the perineum with each thrust -- my G-spot -- drawing a gasp each time he does it. At the end of the kiss, he moves down, and starts to chew on my right nipple; not lick, he's actually bighting me. This is a total turn on. I begin to pant, and to moan. Finally, he moves down further, spits on his fingers, and takes my dick in his mouth, while probing my very tight hole. It has been some time since I've been fucked, and I'm not sure how this is going to feel, but once he's entered me, and started to finger-fuck me, I am completely beside myself, completely incoherent, completely obliterated, which is what the best sex is always about. Probably three minutes of this, and I blast in his mouth, filling him with more spunk than I think he thought I had left in me today. By the time we're done his mouth is dripping -- he hasn't been able to swallow it fast enough.

"Wow," I exclaim after a couple minutes. He's now on top of me again, hugging me.

"You can say that again." Nathan's voice, which surprises both of us.

Jason rolls off me and we look across the room to find Gary and Nathan sitting in the two wicker chairs just inside the door, naked, watching us intently. Nathan's dick has plumped up, and he giggles.

"Sorry," Gary says, apologetic. "We got out of the shower and came in here for our clothes, only to find the two of you going at it. Didn't want to disturb you."

Jason and I look at each other for a moment, and then start to giggle.

"Guess it's our turn for the shower," I say, still giggling.

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We have lunch at a sea food restaurant in Santa Cruz that's just okay. Nothing special. Gary isn't really sure where to find good food here, either. He confides that the best food is from Nathan, who I know is an excellent cook, and that they usually come down with groceries from the Asian markets in San Jose because the Asian markets here are pretty limited. They don't eat out much. Why should they?

The ride home is uneventful. Nathan is "fucked-out," he says, at least for the moment, so there's time to get back to San Jose before his urges conquer him once again. He's only got 24 hours on this green marble, and plans to use them well, but says he "has no juice left," whatever that means. When we get to their place, we all hug cordially, and then Jason and I climb into my car, and make out way home, Jason driving.

I'm giggling again, and Jason glances over at me, looking quizzical. "What's funny?"

"What's not," I ask?

He laughs. "Yeah. That was an interesting couple of days.

"And, did you enjoy it," I giggle?

He pauses for a moment. "I guess, although I really prefer sex with just you." He smiles at me. "With Gary and Nathan, it's like we're all just getting each other off. With you, it's like I'm the most important person on the planet. You make love to me."

"I try," I say, leaning over and kissing him on the cheek. "And you are the most important person on the planet...to me."

He looks at me quickly, tearing up, but regains control quickly, wiping his eyes. Then he snorts. "I was thinking, this morning, as the four of us were spread out on their bed, I was thinking about the last nineteen years. Who would have thought that I'd be having non-stop sex with three other people? Certainly not my parents. I know it's pretty common for children to say that their parents never have sex, and to get sort of grossed out at the idea of it, but I really think my parents had sex only once, and I'm the outcome." He laughs. "Too less sensual people you'll never meet. They never kissed in front of me, never even hugged. Never showed any emotion at all that I can remember, other than anger. They never, NEVER mentioned sex to me. It was an embarrassing, off-limits topic. And yet here I was in a bed naked with three other naked people, three other naked men, getting jerked off. It's just too surreal."

I chuckle. "So, what kind of a kid were you?"

"Nerdy," he replies, instantly. I was a geek, a nerd. There might as well have been adhesive tape holding my glasses together. I guess I was pretty obviously queer, or at least it was obvious to everyone but me, because I got called a lot of names. I don't know. It was one of these "Queer or Asian" deals. People didn't know exactly what to make of me, didn't know whether my mannerisms were because I was queer, or just "foreign." That's a reaction I still get a lot."

I laugh.

"There is something to that, you know," he says seriously. "The whole thing about not being able to tell one black guy from another, or one Asian from another. It depends on what you're accustomed to. When I first came to this country, I'd never seen a Caucasian before. I couldn't tell you guys apart." He looks a little shamefaced.

I giggle. "Yeah, I know. I...honestly...I couldn't tell you guys apart either. We think we're integrated in California, we think we're so very cosmopolitan. It's bullshit."

We're silent for probably five long minutes.

"You know it's punishment night."

"I know," he says, smiling.

Long pause. "But I don't really have anything to punish you for."

He looks dejected, then angry. "Then make up something."

I look at him for a long time, just starting to get him. "Okay. Umm...six of the razor strop and two of the cane."

He snaughs. "What's that? Twelve of the razor strop and six of the cane."

I look at him, incredulous. "But, that's severe punishment. You haven't done anything to piss me off that much."

"I think we need to re-boot you. 12 and 6 should be light punishment," he says. If I'm disobedient, that should warrant something more."

I stare at him a long time. He continues to drive, and doesn't look at me.

"You're kidding, right?"

He looks at me, quickly. "No. I'm not kidding." He looks at me again. "What's the point of this, otherwise, Tim." He begins to tear up, again. "I'm in love with you, and you express love in this way" I want to suffer a little. I was brought up Catholic -- well, sort of Catholic. The point of those `Hail Marys' is to pay back for your sins. It's penitence. I want to be penitent. I love you, but you've got to be firm with me."

I don't know what to say. "Okay, it'll be 12 and 6, and I'll devise something else next time.

He smiles -- broadly -- "Cool. I'll look forward to it."

When we get home, he strips in the entryway, and makes his way down to the basement. I follow a couple minutes later, having dropped off our bags in the bedroom -- his job. He's already in place, on the table. I strap him down. Diving under the table, I also hook a parachute ball stretcher to his ball sack, which surprises him, and I think hurts a little; he grunts a bit as we snap it closed. Good. He needs to know who's in charge. I hang a three pound lead weight from the ball crusher, and that definitely hurts. He groans, starting to complain.

I go to the back wall and retrieve the razor strop, returning to the punishment table.

"You said twelve, I believe, and six with the cane. I don't think we're going to do that. I think we'll do the full 18 with the razor strop."

Jason hates the razor strop. It hurts him the most, apparently. I, on the other hand, I hate the cane because it can leave scars. The last thing I want to do is scar this beautifully creamy skin. Jason knows that he has no grounds for complaining either about my instrument of choice, or about the weight hanging from his balls -- weight that's really going to torment him as the spanking gets underway, jerking from side to side as he does. He looks extremely apprehensive, gulps. "Okay."

I give the strop a couple experimental swishes through the air, and then lay into him with five strokes in a row, very hard, very fast. His ass is already crimson, and he's already crying. I give him five more, same velocity, same speed. He's sobbing now, trying to catch his breath. I give him two more, same intensity but more slowly. "Please, Tim, please switch to the cane."

"Nope. But what I will do if you ask me is forgive the next six strokes. You don't have to take them if you don't want them." This is my way of making the point that punishment is on my terms. 12 and 6 is too much for everyday punishment. He's had 12 strokes so far, and his ass is starting to bruise. I'd said 6 and 2 at the outset. Far more reasonable. "What do you want to do."

He's still sobbing, still panting, thinking. "Please, Tim, could you forgive me the last six strokes?"

I bend, and kiss him, whispering in his ear: "Next time, it might be a good idea to let me figure out how many strokes you should get." He sobs, and continues to sob as I unfasten him and carry him up to bed, cuddling with him after laying him on the comforter.

"You okay."

"Yes," he says, through his tears.

"So, why are you still crying?"

He giggles a little. "Because my ass really hurts -- and because I was stupid...again."

I lean over and kiss him. "It's okay. Your ass will feel better in a couple of minutes, after I put some ointment on it." Reaching into the night stand, I pull out a tube of lotion, squirt some onto my hand, and spread it on his ass. He begins to quiet down.

"As to the stupidity part, I don't just express love by punishing you. Sometimes I express love by fucking you silly, as I hope to do later tonight. Sometimes I express love by accepting the best blow job I've ever had, like this morning. Sometimes I express love by giving you things. And, sometimes I express love by telling you I love you. (I do love you, baby.) Don't look to maximize the love by maximizing the punishment. If I'm not showing you enough love, tell me, because I couldn't love you any more."

He's sobbing, and has attached himself to me, hugging me so hard I can almost not breathe. "I'm...so...sorry," he says between sobs.

"It's okay. You just keep trying to be in control. You have to give that up. You're mine."

"I know," he wails, still strangling me.

Eventually, he stops crying, and we snuggle for maybe an hour before it's time to start dinner.

He really is adorable, and I am really...irrevocably...in love.

Next: Chapter 10


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