Shooting on a Bet

It happened on a Saturday afternoon. I had left the health club after a good workout and had walked over to a pleasant gay bar near a notorious leather bar. I was with a good friend, my workout partner, Tony. We were met at the bar by two of the health club fitness instructors, Bill and Steve. The four of us liked to get together on Saturday afternoons, when the bar usually was empty. We'd shoot pool, drink some beer, listen to rock 'n' roll, and have a few laughs.

The bartender on duty was Hank. He first saw me one Saturday afternoon about a year earlier sitting on a barstool, my back against the bar, watching the pool shooters. He had come up to me, pressed himself in between my legs, rubbed my thighs through the fabric of my jeans warmly with firm palms, and said, "What great thighs you've got, man. I'm Hank. I get off in 45 minutes. Come home with me."

I said it would only be for sex. He had laughed, saying, "All right!"

Hank was an imaginative lover, with humor, strength, and staying power. We got on well, even though we were unable to get together often because of other commitments we both had. We were solid friends.

This Saturday, after playing a few racks of pool, the five of us found ourselves together at the bar, talking about this and that, when somehow the conversation got around to masturbation. Knowing my fondness for the subject, and my inclination to practice the art whenever I feel the need, I was most likely the one who turned the conversation to it, but I don't remember exactly. As it turned out, I wasn't the only one who liked the subject. We all liked it. A lot!

"Bullshit," Steve was saying, "only teen-agers can do it three times a day." He was unconsciously rubbing his crotch as we fell into this heated discussion.

"Com'on, Steve, grow up," Bill said, laughing, "I can cum three times in one day without effort."

"But you don't, do you," Steve countered. "I'm talking about beating off every day, three times a day. No one can do that."

"Oh, I don't know," I said, "I did it for more than ten years straight. But is frequency so important? It's quality you want when you need it. Don't you think so?"

"Yeah, that's right," someone agreed.

"Okay, sure, Jack," Steve said excitedly to me, "but you didn't hear what Tony was saying to us. He said that he still beats off three times a day, every day!"

My head snapped around and I looked at Tony in amazement. I had known him for three years and had seen him naked several times each week, showering with me at the health club, and had never seen a hint of an erection from him. He had always seemed quiet, modest, shy and, well, sexy, but not aggressively so. I wasn't even certain he was gay. A new respect for my old friend bloomed.

"Did you tell him that, Tony?" I asked, looking into his dark eyes, wondering why he had decided to be so candid about his sex life.

"Well I only told him that, Jack, after I told him you said that you hit the headboard every time you jack-off." Some of his words seemed slurred.

"What?" three people chimed in together, including me! Hank started to laugh.

"Shit, Tony, you told Steve that?" I laughed, throwing my head back, enjoying the surprised looks on their faces. I thought, Tony didn't eat lunch and these beers must have gotten to him. But I remembered that Tony and I had had a brief conversation about masturbation a few weeks earlier. Somehow it had gotten around to distance and I did claim that when I jack off on a bed and do not control the aim, my cum hits the headboard.

"Fuck, Jack, it looks like he's just told everyone," Steve said with a laugh. He leaned in closer, leering at me, and asked, "Is it true?"

I hesitated, watching them. Steve's hand had worked up a large bulge in his trousers. He was enjoying this. Hank's eyes were on all of us, taking this in excitedly from his side of the bar. Bill was watching me with anticipation, and Tony had a vague smile on his face, as if to say, Get yourself out of this one.

"Com'on, Jack," Steve persisted, "is it true? Can you hit the headboard every time you jack off?"

I smiled.

"I don't believe it!" Bill said, emphatically.

"Me neither," Steve said, "not even teen-agers can do that." He must have a real fixation on teen-agers, I thought.

I kept smiling.

"I'll bet money he can't do it," a voice said from the other end of the bar.

The five of us turned to look down at the intruder. He had been sitting there quietly since we came in, but I hadn't taken notice of him.

When he saw us turn towards him, he got up, took his beer glass and started down the bar. I looked around and saw that there was only one other guy in the bar, a young guy named Mark whom I had shot a few games of pool with before but didn't know well.

"Maybe teenagers can hit the headboard, but grown men like yourselves can't," the newcomer said, looking directly at Steve, then directly at Steve's bulging crotch. He smiled.

"My name's Paul," he continued, "and I'll wager $50 that none of you could hit a headboard."

Silence. We all watched him as he came towards us. He was well built, tall and confident, carrying himself with grace. I liked him.

"You're on!" Tony blurted out.

I laughed and said, "Wait a minute. Wait a minute. No one is 'on'. We're not going to take a bet from this guy, Tony. How'd you ever prove you won."

"That's easy," Paul said. "Hank will lock the door for 15 minutes, we'll put something down on the floor, we'll watch the guy cum and see if he hits above his head. Simple," he said confidently.

"Yeah, that's it," Tony said, "you can lie down on the floor and jack off, Jack"

I felt like strangling him, but I couldn't stop laughing.

"Wait, I'm serious. Don't laugh," Paul said looking right at me. "I'll bet you one hundred dollars that you can't hit over your head when you cum."

Silence. I kept smiling.

"Good," Tony said, "let's see your money. Hey, Steve, want to get in on this bet?"

I couldn't believe the way Tony was behaving. He pulled out his wallet and started counting out bills.

"Tony" I asked, "what are you doing?"

"Hey, I'm covering the bet. You said you could do it, Jack. So do it."

"Right here?"

"Why not, we're all friends. We all beat off. We all like to beat off. I think we'd all like to watch someone beat off. I know I would. In fact, I'd like to watch YOU beat off, Jack." He smiled at me. He wasn't drunk at all. He was turned on! He was challenging me to put up or to shut up. The money didn't make any difference.

"Yeah," Steve said, fondling the bulge he had developed. "I'd love to watch you jack off, man."

"Geez, me too," Bill agreed. "I'd even do it with you." He started rubbing his crotch suggestively, openly in front of us, spreading his thighs, thrusting his hips forward, and fingering his growing erection. The light-hearted atmosphere changed to a sexually charged one with the seriousness of his hand movements.

"I'll lock the door," Hank called out as he moved toward it. He smiled confidently back at me, letting me know he liked the idea. I had known he would.

"Wait a second, Hank," Paul called to him, "I've got a thick car blanket he can lie on."

"Naw, that's okay," Hank said, putting out his "Back in 10 Minutes" sign and locking the door, "we've got a couple good ones under the bar for just such an occasion."

"You'll do it then," Tony said. It wasn't a question.

My groin started churning. The idea of jacking off in front of these men was turning me on.

"There are several conditions," I said firmly.

"Oh, here it comes," Paul remarked sarcastically, expecting me to weasel out of it somehow, "what are they?"

"Well, we all have to get naked. I'm not going to be the only one."

"Great!" Bill said.

Everyone seemed to agree. I looked over at Mark. He had moved closer and nodded agreement with a sly smile. He stood up and came over.

"What else?" Paul questioned, a less sarcastic tone in his voice.

"I want something absorbent, like cardboard, above my head so there won't be any question that my cum hits it." I smiled as they quieted down, looking at me. They realized that not only was I serious, I expected our side to take the money.

"Wow," said Mark.

"Oh. Well that's reasonable. Sure," Paul agreed, smiling now. "How about some of those posters out at the front entrance? What do you think, Hank?"

"Here are some old, stiff ones. Good size, too," Hank said, pulling them from under the counter. I was beginning to think this had been all set up for me, but I was enjoying it.

"Com'on," Tony called, "let's get it started. Here's our $100, where's yours?"

"I'll hold it," Hank said, taking money from Paul and from Tony. "Okay, Jack, I guess you're on."

A blanket had been lain out on the floor like a narrow cot, and at the head of it several large posters were leaning against the wall, the cardboard backs showing, in imitation of a bed's headboard. The seven of us formed a semi-circle, tensions mounting.

"Want some help with your clothes," Mark whispered seductively. He started unbuttoning my shirt. I didn't stop him.

"Yeah, here, let me help," Tony said, and knelt at my feet, pulling off my shoes and socks.

I smiled. "You heard the rules, fellows. Everything off," I said, letting my shirt be pulled off of my stocky shoulders, my bare, well-developed chest coming into view.

"Hot damn," Steve said. "I'm going to like watching this." I could see that he was fully erected, the bulge in his pants straining to the waistband. He took off his shirt as mine came off. He had the best build of the fitness instructors at the club, and his naked chest and muscular stomach caused the others to look at him admiringly. I felt more comfortable with him there, drawing attention away from me. And watching him strip was a turn on for all of us.

My fly buttons were being popped open and my jeans slid down my legs.

"He's not wearing shorts," someone whispered.

"Geez, look at that cock," Bill blurted out in awe. He had stripped down to his jockey shorts, a large bulge displaying his eagerness to participate.

My cock was partially inflated, not fully erect. It looked big, dangling there above my large balls. I rubbed my crotch, fluffed up the hair, scratched my balls and hefted my cock in my left hand, showing it off.

"Looks like I'm almost ready," I said, "how about you guys."

Mark had his hand on my ass, presumably using it to balance himself as he pulled off his jeans. Bill was playing with his cock through the jockey shorts, waiting for the others to finish undressing. Steve, his bulging thighs and washboard abs the envy of all of us, was standing at the foot of the blanket slowly stroking his handsome erection, a long, blunt, cut one, his balls swaying easily beneath the pumping hand. Hank had stripped quickly and was bringing his long, uncut beauty to attention with loving caresses. Tony stood across from me, naked but shielding himself from my view behind Paul, who had quickly undressed to reveal a mature, trim and fit, handsome body with a large, fat cock, playing with it as he studied me.

"Let's go," Hank directed, a catch in his voice showing his excitement.

I stretched out on my back on the blanket, head reasonably near the cardboard, and got comfortable, staring up at Bill and Mark on my left, Steve at my feet showing off his cock to me as I looked at him, Paul and Tony on my right.

Hank knelt down, next to Tony, at my head and asked me, "All set, Jack?" He started playing with his erection next to my face, offering it to me. I sensed that he wanted to help get me real hot so I'd shoot a forceful load.

I looked up, after grabbing my cock and starting a slow masturbation, and loved the scene of these six sexy men around me in various stages of developing arousal. After three careful strokes, my hot meat was primed, fully erect, ready to go.

"Man," Tony said, a clear note of awe in his voice. "Look at the size of that cock." I watched him and saw as he turned towards me, out from behind Paul, that his hand was filled with a whopper. It was the largest one in the standing group with no doubt, and easily matched my own. I had never suspected he had such a big one. I grinned at him, staring up past his huge cock. He smiled down at me.

"Shit, this is getting me hot," Mark said. "I'm about ready to shoot a load."

"Be careful," three guys yelled out. One continued, "don't let your cum hit the headboard."

"When you cum," I instructed them, "aim for my cock and balls, that would really be a blast for me. Shit, fellows, you can't imagine how sexy it is, what a turn on it is, to look up at you guys jacking off over me. I don't know when my cock has felt this hot!" I moaned, rolling my hips, flexing my buttocks and thigh muscles, my left hand playing with my hard nipples, rubbing my chest, my abdomen, my cockhair.

"God, that does it," Mark cried out softly, "I'm coming!" and we watched as he flexed up onto the balls of his feet, thrust his hips forward and let fly a long string of cum. It arched upwards and fell directly on my pumping hand.

"Good man," I smiled at him. More of his cum flew towards me, landing on my balls, my thighs, and my calf. Mark relaxed but kept pumping his stiff cock - he was going for a second load.

Out of the corner of my eye, I saw that Bill was starting to shift his hips around with sharp, short jabs. His well-formed, large cock was being pumped rapidly into his tight fist, his eyes half-closed, watching me pump my hard shaft, now shiny with Mark's cum.

"That's it, Bill, pump out that load," I whispered up to him. My left hand went out and touched his knee, pressing up to his lower thigh, straining to touch his scrotum.

"Ugh," Bill grunted, "I'm coming!" and he pushed down on his cock, aiming at my groin. Nothing happened for a moment. We all were staring at his heavy, fully engorged deep red cockhead, when suddenly he came so strongly that it almost looked like he was pissing, one heavy rope of sperm jetting out after another. His aim was great and his hot juice warmed my hand, cock, balls and abdomen.

Steve, who had been trying to play it so cool, but who had been unable to take his eyes off of Bill from the time Bill pulled off his jockey shorts, started to groan. His technique for masturbation must have included isometrics, for every muscle of his beautiful body looked enlarged; every curve in his musculature was sharply defined. His balls were pulled up tight against the cockbase. He was ready.

So was I. I had been watching all of them jacking off, and I had never felt so alive, so hot. The cum that landed on me, lubricating my pumping fist, making my hot cock slippery and shiny, was bringing me to the brink.

"I'm about to shoot, you guys." I said. "Want to cum together?"

"Yes," Steve said. "I'm ready to shoot my load."

"Okay," Hank hissed through clenched teeth, standing next to Tony, rubbing Tony's thigh, fingers playing up onto Tony's balls.

"Say the word," Tony said quietly, "and I'll cum right with you, Jack." He smiled at me, lovingly. He told me in that instant something I had never realized before, he was in love with me. I smiled, and said, "This is for you, then," looking right into his eyes.

"On the count of three, the third down-stroke on our meat" I said.

"One," I said, preparing to aim my cum-shot an inch or two above my face.

"Two," several voices called out.

"Three," we said in unison, as Steve's cum hit my balls with a juicy splat. He had been unable to hold off and came an instant sooner than the rest of us, holding his cock down in an overhand grip pointed at my balls, and letting the heavy ropes of very white cum fly. The splash of his white heat on my balls put me over, and I came in an overwhelming climax.

The first powerful jet of semen, aimed carefully above my head, flew over my face and landed on the cardboard behind my head with a heavy, loud thud.

"Christ!" Paul exclaimed, and his cock erupted with its first spurt of cream. "You hit it! That's great!" He kept up his short strokes and flooded my belly with his cum, not by aiming downward, as Steve and Bill had done, but like Mark by thrusting his cock up into his pumping fist and letting the huge spurts fly straight up into the air, watching me watch them tumble end over end toward my flat stomach, hitting with loud smacks.

My second rope of sperm landed on the cardboard with a louder thud.

"Holy shit!" Hank said and started shooting his hot load into the air, watching it fly towards my navel.

The third spurt from my cock landed right on my mouth. I sucked it in loudly, slurping greedily, lustily. More ropes spurted out of me, mixing with the sperm on my neck, chest and belly.

"Hot damn," Tony cried out, and aimed his erupting stream of cum right at my open mouth. I stared at him as I caught his cum on my tongue. I smiled, swallowed, opened my mouth and caught more.

"Man, this is somethin' else," Mark said breathlessly, "I'm coming again!"

We all watched as he went up onto the balls of his feet. His hips pushed forward again, his cock standing straight up out of his fist, and the cockhead swelling, as cum spurted out, flying higher than before, hitting me on the chest with a loud splat, followed quickly by four more loud cum smacks on my chest.

I was spreading the mixed juices over my balls, my thighs, my cockhair and abdomen, stomach and chest, breathing in the heady, heavy aroma of musky sperm. Aftershocks sped through my glistening, wet body. Cum seeped from my cock, and from cocks being milked down over me, dripping onto me, finishing the shower of cum I was bathed in. It was one of my life's most incredible moments!

Hank knelt down and began sucking on my skin, lapping up the spent semen, and cleaning me off. I could see that Steve wanted to do the same thing, but was holding back, glancing over at Bill from time to time. Paul took the lead from Hank and went boldly to his hands and knees and lapped noisily at my balls, licking up Steve's cum, it seemed to me. He slurped and sucked his way to the head of my still solid erection and slipped his mouth over it, drawing it partially into his throat. He was a very talented cocksucker.

Tony and I just kept smiling at each other. In a crowd, we had found one another.

I laughed, and pulled Paul up off of my sensitive cock, saying, "Whew-ee, man, you better watch out or I'll blast a hole in your throat."

"Fuck!" he grinned at me, "I guess you would." He laughed and rose to his feet, then offer me his hand to pull me to my feet. I grabbed it and jumped up quickly. Tony reached out to steady me and his hand touched my cock. He grasped it, held it, and pulled on it gently. I was still hot as a firecracker.

Not that I was alone. Steve, Hank, and Tony were all completely aroused, sporting throbbing erections. Bill and Mark were showing that puffed up but semi-hard stage. Paul, who was probably the oldest in our intimate group, appeared to have gone rather soft, but he seemed to want to continue the group sexual activity.

He squatted in from of Steve, looked up at him with a pleading expression, and opened his mouth. Steve looked at Bill.

Bill said, "Well, that was great. Let's get dressed." And he grabbed his jockey shorts and started pulling them back on.

Steve put his hand on Paul's head, not to draw it near but to hold it back. He smiled sadly and said, with some kindness I thought, "Not today, my friend."

All of us realized that Bill wanted Steve, but had been unable to tell him so. And that Steve was having difficulty letting Bill know how he felt about him. They all got dressed quickly, but I just scooped up my bundle of clothes and went naked into the men's room to take a standing rinse at the sink, cleaning up completely.

When I went back into the bar, fully clothed, applause greeted me. They were smiling and cheering, yelling dirty remarks at me, having a good time. I felt great.

Paul had retrieved the cardboard poster and it was laying flat on the bar, two long, dark, wet stains running the length of the paper. No one was putting beer glasses on it.

As I went up to them, Paul threw his arm around my shoulder and said, "You're terrific! I'm glad to lose that bet, it was worth the money just to watch you lie there pumping that magnificent cock of yours. Look at this poster. Two huge globs of your sperm hit the mark, I watched as it happened. I had thought a small drip or two might hit it if you were lucky, an initial spurt from the start of your climax, but I never expected to see two full globs fly that far. It must be some kind of record."

I laughed. "Well I guess it is for this bar, but I'll tell you something, did you see Mark, here, let fly? It looked to me like his second orgasm almost hit the ceiling, and if he had been lying next to me, I think he would have split the cardboard in two." I laughed again, but everyone was looking at Mark with renewed interest. He was the only one of us to become so excited that he shot twice, and he had cum first.

He seemed to be the youngest, and he blushed as he heard himself being discussed and then being stared at. His manner took on an "Aw, shucks" kind of air. He looked down at the floor.

"Yeah, that's right," Tony said, excitedly, making me wonder what he was up to now. "I was surprised when I saw Mark's second load sail up above my head. Why I'll bet he can shoot his cum farther than Jack, and I thought Jack would be unbeatable."

"I'll take that bet," Paul responded immediately, a broad smirk on his conniving face, obviously delighted with Tony for helping to instigate another jack-off party.

Hank suddenly said, "Oh, shit, I forgot to unlock the door. I've got a business to run." And he went to open up, changing the atmosphere back to normal.

No one was waiting to come in. I looked up at the clock and was surprised to realize that less than 20 minutes had passed for the whole episode to take place. I decided to leave.

Tony came over to me and asked, quietly, "Want some help with your hand, Jack?" He smiled.

"Com'on, fucker," I grinned, "I need all the help I can get." I put my arm over his shoulder, waved to the others, and headed for the door with my best friend.

"What about the new bet?" Steve called after me.

"Let's talk about it next week," I responded, grinning back at him.

Everyone yelled at once: "We'll be here!"