Master Lucky's Story

by Thom Magister

New York — Summer 1951

Back in the 1950s, long before our crowd became the infamous and legendary “Old Guard,” men who were into leather didn’t define themselves as precisely as they do these days. There were many so-called leather bars that catered to the various tastes and diversions enjoyed by our crowd. For instance, there was a great piss bar in New York with a drain in the middle of the floor to take care of any spontaneous action.

I was sharing a huge garden apartment with my buddy Chuck — actually Charles, but we called ourselves Chuck and Lucky (Lucien didn’t seem to go with my leathers). Chuck did Western and I did biker, and we had very different sexual tastes, so there was no competition between us.

Back then, Masters were just the guys in charge, the ones who took a dominant role in a sexual interaction — and, in some ways, in a couple’s everyday interaction. A slave was usually a hot guy who liked it rough and turned himself over to a Master for whatever the big guy had in mind. A good Master respected and protected his slave. Of course, there were always a few bad apples in the mix, but they were usually straightened out by a good whipping, or possibly a gelding, administered by more respect-worthy Masters.

Chuck was my best friend in every sense of the word. We loved each other and probably would have been sexual partners if our tastes had meshed, but they didn’t. I remember the first time I saw him. He strode into the bar looking like he’d just hitched his horse outside. He pushed his cowboy hat back and let his blond curls fall out around his forehead. He made me think of an angel gone bad, and I wasn’t far wrong. In the months that followed we got to know each other and decided for the hell of it to live together.

Of course, as a cowboy his particular skill was bondage, and he could rope and hogtie a guy in a matter of minutes. I was in awe of his skills. I was your basic “Whip ’em and fuck ’em” leatherman. I took care of several guys on a regular basis, and they took care of me. I never really thought about the whole slave thing until I met Alan.

Chuck and I were having an afternoon beer in one of the Village leather bars that summer in ’51 when this old guy came in with two young sailors. It was Fleet Week, and the city was crawling with cute boys strutting around in summer whites that molded to their butts. Chuck looked at me, and I knew exactly what he was thinking. We waited until the old guy went to take a piss, and then we grabbed the two sailors and dragged them out of the bar and back to our place.

Now, back in those days almost all young guys professed to be straight. If they showed up in a gay bar, they were typically “trade” who could be had for money or just wanted a blowjob. No doubt many of them really were horny straight guys looking to get off in a willing mouth, but some, like Alan, had yearnings that extended way beyond that.

Chuck took his sailor into his bedroom, and I took Alan into mine. He was probably only 19, a few years younger than me, and his round ass stretched his whites to the limit. His bright red hair and green eyes reflected his Irish background, while his dark skin and cheekbones were a gift from his Cherokee Indian heritage. He had a smooth, hairless body and a cock that belonged on a horse. He stood at attention as if he expected me to bark orders at him, and his large, brown nipples stood out on the planes of his chest.

Alan watched me as I inspected his body, and when I ran my hands over him, his thick cock bobbed up and down with each caress. He was about 5'10" — just slightly shorter than me. My own dark Italian coloring and stocky build were in sharp contrast to his slim build and exotic coloring. His cock was cut; mine was not. And my body had more hair, beginning with my thick pubes and traveling in a thin line up my stomach and then across my chest. His mouth was full and perfectly shaped, with a classic Cupid’s bow upper lip. I wondered if he even shaved because there was no trace of a beard — I always looked as if I needed a shave. If it’s true that opposites attract, then we were certainly a good example.

We could hear noises coming from Chuck’s room — I figured his sailor was learning a new meaning for “ride ’em, cowboy.” Alan looked nervous. I grabbed hold of his thick cock and squeezed until he winced. I pulled on his balls, then reached around and smacked his ass. He offered no resistance.

While I worked his nipples long and hard, he constantly pushed his chest up into my hands, begging for more. His cock was swollen, the head flushed bright red. I reached down and smacked it lightly and then harder until it jumped and bobbed and pushed out precum in long, drooling threads. I smacked his ass, pulled his butt apart, and touched his hole. He flexed and didn’t try to stop me.

“You like that, don’t you, sailor?”

“Sir, yes, Sir.”

“Would you like more?”

“Sir, yes, Sir.”

“You have a nice cock.”

“Sir, if you say so, Sir.”

“And a great ass.”

“Sir, if you say so, Sir.”

“Would you like me to fuck your ass, sailor?”

“Sir, does this sailor have a choice, Sir?”

“No.”

“Sir, very good, Sir.”

I slid my black leather belt out of my jeans and whipped his ass.

“Sir, should I count, Sir?”

“If you like.”

“Sir, very good, Sir. That was five.”

I whipped his ass until the count reached 25. The cheeks glowed red and were hot to the touch.

“Grab your ankles, sailor.”

“Sir, yes, Sir.”

I spit on his hole to lubricate it. I squeezed some K-Y into my palm and coated my cock with it. Then I moved into position and eased slowly into his hole. He opened up and took me in. I wondered if he’d been getting fucked regularly by his shipmates.

“Are we good, sailor?”

“Sir, yes, Sir,” he said and pushed back onto my cock.

I grabbed his hips and drove into him harder and harder, watching my cock move in and out of his pink hole until I felt myself near orgasm. I pulled back and smacked his glowing ass. He moaned beneath me and pushed back to drive my cock deep into his ass. I reached around and grabbed his cock. His balls were swinging free below it. I moved my hand, still slick with K-Y, along his shaft in the same tempo as my fucking.

“I will order you to come, sailor. I expect you to obey that command. Are we clear?”

“Sir, crystal, Sir.”

I pounded deep into him with every thrust and let his thick cock slide back and forth through my encircling hand. I held back as long as I could and then ordered him to come.

“Now, sailor, come now!”

“Sir, yes . . . ,” but he didn’t complete his response as his cock shot out his load and the muscles inside his ass grabbed my cock and drained my cum into him. He didn’t move.

“Sir, thank you, Sir.”

I looked down at his beautiful ass. It was so round and hard and perfectly shaped. I could spend hours inside that hot hole and never get tired of fucking it. His ass was clenched tightly around my cock, holding me tight.

“Relax, sailor.”

“Sir, may this sailor have a few more minutes, Sir?”

I stayed inside his ass and ran my hands over the sensitive surface my belt had marked. I ran my hands up his back and massaged his shoulders. I reached under him, lightly brushed his nipples, and again took hold of his cock, which was still fully erect.

“Sir, thank you, Sir.”

He relaxed and allowed me to pull out.

“At ease, sailor.”

He stood at parade rest.

“Sir, permission to speak freely, Sir.”

“Granted.”

“Sir, this sailor loved that fuck, Sir.”

“You’ve got a hot ass, sailor.”

“Then I pleased you, Sir?”

“Oh, yeah.”

“Sir, permission to return to you, Sir.”

“Alan, you can bring that sweet ass over here any time you want. But enough of the Navy formalities. They’re fun when we’re fucking, but knock it off now.”

“Yes, Sir — sorry. Yes, Lucky.”

I flopped down on the bed and beckoned him over. He sat down and curled up in my arms. I lifted up his chin and kissed his full lips. They were soft and moist and very inviting.

“I’m not used to being kissed,’ he said.

“Why is that?”

“I usually just get fucked.”

“And that’s okay with you?”

“I like to serve a man and please him. If he gets pleasure from my ass, then I’m happy.”

“Have you been fucked a lot?”

“Eight times including today.”

“How long is the fleet in town?”

“Three days.”

“And you guys are on shore leave?”

“Yes.”

“Do you have to report back every night?”

“No. Not until Friday at 8 bells.”

“How would you like to stay here with me?”

“Very much, but what about my friend and your friend?”

“I think they’ll work something out.”

“Sir, may I serve you again, Sir?”

“Oh, yes, as much as you want.”

Alan’s capacity was amazing, and for the next few days we explored every possible way a man could be fucked. He never seemed to get enough, and I worried that when he left me that hungry hole would get him in trouble. He was shocked when I would suck his cock or tongue his sweet pucker — these were new, unimagined sensations to him. He slowly learned to kiss, but he never really liked to suck my cock. I think he preferred it in his ass, and so did I.

On our last night together, he did everything he thought would please me — even sucking my cock for quite a while before we went back to serious fucking.

“What happens now?” he asked finally.

“What would you like to happen?”

“I’d like to jump ship and stay with you.”

“Not a good idea.”

“Yes, Sir, I know.”

“How much longer will you be in the service?”

“About six months. Then I can re-up if I want.”

“Do you want to?”

“Well, I don’t have any real professional skills, so the Navy is a good place for me.”

“That’s one option.”

“May I come back to see you when I get out?”

“Yes, I’d like that.”

“May I write to you?”

“Sure.”

“Will you answer?”

“Of course.”

“Then I think I’ll be able to hold myself in reserve for you — if you want.”

“Alan, that would be terrific.”

The next six months went by quickly. His letters came almost every day, and I enjoyed all of them and responded as often as possible. I wasn’t sure what he intended to do, if he would sign up for another hitch or not. I hoped he wouldn’t. And then he was standing in my doorway in his winter blues and holding his seabag.

“Welcome home, sailor.”

He threw himself into my arms and kissed me deeply. He looked bigger and stronger and strangely sure of himself.

“Good to be back, Sir.”

“The Navy appears to have been good to you.”

“Yes, Sir. I decided to build myself up in my spare time. We had a weight room onboard ship this time.”

“Did you re-up?”

“Not yet, Sir.”

“Why not?”

“I wanted to see you first, Sir.”

“Do you want to talk about that?”

“Could we fuck first, Sir? It has been a long wait to be with you again.”

Our first night back together was again amazing. I think we fucked for six hours straight without a break. Chuck peeked in to see if we needed anything, then took off to find a new stud to rope. Alan’s body was thicker and more muscled than before, and his ass had become rock hard. I could bounce a coin off it. We finally came up for a break.

“Sir, you have made this sailor very happy, Sir.”

“Okay, sailor, at ease.”

“I missed you, Lucky. I thought about you constantly. I just wanted to be with you again, and not letting anyone else touch me became like a gift I could give you. I want my whole body to be yours to use for your pleasure — and mine. I want to devote myself to you. Is that crazy?”

“Well, it makes my cock hard, if that answers your question.”

Before Alan moved in, Chuck and I both felt there had to be more than what we were doing, just fucking around with one guy after another. We wondered if our friendship kept us from forming other attachments. Was there a way to have it all? And then the answer came — not from Alan, but from a guy named Jason.

Chuck had dragged Jason home one night, hogtied him, and fucked him until the rafters shook. The action was so heated that one of the pictures on our adjoining wall shook loose and crashed to the floor. They kept at it for three days. At one point Chuck came out and asked if I knew how to fist someone. This was the ’50s, and fisting was a dark secret. I didn’t know and told him to follow his instincts. Apparently that worked, and they continued to move the earth together. I think Alan was both fascinated and intimidated by all the racket. I wondered if he felt envious of Jason. Maybe I wasn’t fucking him hard enough.

Chuck and Jason finally emerged one morning looking like they’d been through the wringer.

“Some ponies can’t be broken,” Chuck said with a shrug. “You just gotta ride ’em and show ’em who’s boss, but that isn’t easy.” Jason smiled, very pleased with himself. “But I broke ’im, and now he’s all mine.”

I looked at Jason to see if he agreed, and it was obvious that he did.

“What’s your secret, Chuck?” I asked.

“I think the answer is picking the right mount. Ya gotta find the one that wants to be broken but puts up a fight. They don’t go gently.”

“Jason, would you like to share your view?”

“I look at it this way,” he said. “I’m built to be fucked and know it. But I’m no one’s easy piece of ass, and I’m not a sucker for every guy with a big cock. I want a man who will do two things — work me hard and take care of me.”

“You want to be kept?”

“Hell, no. I want to be owned.”

“Owned?” I asked, frowning.

“Not bought and paid for in the usual sense,” he said, “but if I turn myself over to a man, I want him to think of me as, well, his treasure. I want to see lust in his eyes, but also respect and appreciation. I want him to see me the same way I see him — but from the other side of the coin.”

“That’s a lot to ask for.”

“Not if you deserve it.” He looked over at Alan. “What do you think, Alan?”

“I think you’ve described me really well. I never put it together that way myself, but I certainly relate to it when you lay it out.”

“So,” Chuck grinned, “are we a foursome?”

“I’m in,” said Alan.

“I might as well make it unanimous,” I said.

In the weeks and months that followed, Alan became more and more loving and devoted. I saw him, as Jason had suggested, as a wonderful gift and a cherished possession that needed to be loved and protected. And while I struggled with my seemingly opposed desires to protect him and to plunder his beauty as often as possible, I slowly came to realize that he wanted all that as much as I did. He wanted to be whipped and fucked and then held and cherished. Every time we reached an impasse, Jason would step in and talk us through.

“Don’t question what we do,” he said as he looked at us sitting around one evening. “The only thing that matters is why we do it. Think about a kiss. We all have very positive thoughts about a kiss. So a kiss is a good thing. But what about the Judas kiss? Not a good thing. The difference is intent, as it is with everything.

“Lucky, when you whip Alan’s butt you cause him terrific pain, but your intent is to give him pleasure because you know he wants it. Trust me, he wouldn’t enjoy it if a stranger did it. And because he knows that it pleases you to whip him, it doubles his pleasure. And since you know he likes a good workout on his pretty butt, you can whip him without feeling something is wrong.

“Some guys think it’s crazy to want a fist up their butt, and it probably isn’t really sexual in the strict sense of the word. But look at the amount of trust between the guys who do it. That is hot. Men, trust is an aphrodisiac — it’s better than drugs or booze. I look at Chuck, and my trust in him opens me up to everything he wants. It frees me. And okay, I’ll say it: it frees me to be his slave.”

There it was finally — he’d used the word we hadn’t dared say aloud: “slave.” I liked what Jason put out. Thinking of it that way allowed me to do many things with Alan that I might otherwise have hesitated to do. Eventually we met other men in similar partnerships and often got together to explore the dynamics that made our interactions work. Jason had opened the way, and while he continued to coach Alan, Chuck and I often talked about what was happening to us.

Sometimes I’d take my time whipping Alan’s back and ass, and by the time they glowed hot and red he was driven crazy with wanting my cock inside him. But I’d take my time and enjoy his ass until I was so hot and my cock was so dripping that I just had to fuck him. We liked to start it slow and even, building up to hard and fast until he was bucking and pushing me deeper and deeper inside him.

Sometimes I liked to put him on his back and lick his armpits and suck his nipples. He knew the drill — no moving. I worked his nipples until he started making those little whimpers that I loved, and then I’d suck his cock and balls, which he professed not to like but I know he did. I always took my time with everything, because we were partners and time was ours to spend.

I’d roll him over with his cock in my throat and play with his ass, which made him buck in my throat. Sometimes I’d fuck his face, which he accepted and finally got to like. And there were always those long kisses that drove us both crazy. At night we almost always went to sleep with my cock deep inside him and my arms wrapped around him and my lips kissing the back of his neck. And sometimes he’d put on his sailor suit and we’d remember those early days.

“I’m going to fuck your ass, sailor.”

“Sir, yes, Sir.”

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