James Grady

Jerking his seven-inch uncut cock while dragging on a cigarette and sipping a shot of whiskey in the backyard shed was 18-year-old James Grady’s reward to himself after a long day’s work. He had his ritual of sitting on a low wooden stool, undoing his trousers and peeling back his foreskin. Being medium height, thin, brown-haired and brown-eyed, he was a good-looking young man.

His mind was flooded of images of the men he was fascinated with. There was Donny, the boy he adored when he was 14 before he left school. Tall friendly Officer Bolton, the good looking neighborhood beat cop. Mr. Leary, the older burly and often cross mailman. The construction workers he observed.  From going to the movies there was Clark Gable, Gary Cooper and Cary Grant. There were so many more men he thought of as he stroked his throbbing cock. He thought of their masculine faces, their beefy bodies and imagined what their cocks were like.

In 1934 Brooklyn, fairies and queers as such bad men were called, were mocked, despised and going to hell. He’d heard of such men and realized in his heart that he was one of them. Then there were the comments he’d heard boys in the street meanly say about others, “He’s a cocksucker for sure.” “He takes it up the ass.” 

When he was in school before his mother pulled him out at age 14 to help in the rooming house, he recalled crude vague tidbits from other boys about girls. His mother had never discussed such things with him. 

As his cock shot off, he thought as he often did of beautiful Donny. James spilled his jism on a rag and tossed it in a bin. Since, he did the laundry his secret was safe. It was because of Donny, that James was first moved to jerk himself years ago without quite understanding why, he just knew that it felt so good to do. Now, he was aware of what it was all about and yearned to be with a man someday.

His day began at 5:00 AM when his widowed Irish-immigrant mother Nora woke him up. She was 37 and was a trim strong woman whose brown hair was starting to go gray. Her husband Michael, a construction worker had died in an accident 13 years ago. Luckily, he left his paid-for family house which Nora turned into a rooming house.   

James delivered The Daily News to local houses and apartment buildings. He returned home and helped Nora make the batch of sandwiches that he sold at lunchtime at a nearby construction site to the workers. Back home, he did the laundry for the residents of the rooming house and for various neighbors. He’d boil pots of hot water, wash the clothes and dry them on the backyard clothesline. Then fold them, put them in baskets and then bring the baskets to the people.

By then it was late afternoon and off to the shed for his pleasure. His mother didn’t want him indulging in that filthy habit, so he had one covert jerkoff cigarette with a shot of whiskey.  

“A bath? I took one yesterday” said James to his mother when he entered the kitchen of the rooming house she ran. “Never mind! Just do as I say.” 

The dwelling was two stories. The three upstairs bedrooms were rented out to tenants. Miss Dennis was a librarian and Miss Sloane was a schoolteacher, they’d each been there for a few years. Mr. Johnson, a retired bus driver had moved out last week to go live with his daughter. He was replaced by Mr. Parker, a 28-year-old man who worked in a local bank. James’ mother slept at night in the living room, and James slept in a small room off the kitchen.

“There, don’t you look nice and clean” said Nora, as James appeared after his bath. They were in the kitchen. “Tonight, after supper you’re to go to Mr. Parker’s room. You do whatever he tells you to do. He’s a good man.” “Yes, ma.”

The weekly rooming fee included dinner and so Miss Dennis, Miss Sloane and Mr. Parker ate in the dining room, while Nora and James ate in the kitchen. “But, I’m hungry” said James. “I’ll fix you something later.” After their tenants had finished and left, James cleared the table and washed the dishes. “Well, you’d best head upstairs” said Nora. James was confused but trusted his mother as always, that something which would help them was involved.

“Come in, James” said the smiling handsome and mustached dark-haired Mr. Parker. He wasn’t wearing his suit anymore, instead he was in a white tank top and white underwear with buttons in the front. James noticed his strong arms and the bulge below straining at those buttons.

“Have a drink” said Mr. Parker as he handed James a glass of whiskey. “Thanks, Mr. Parker.” Sit.” They sat across from each other, sipping whiskey.

“Your mother is a fine woman. Keeping things going in these times on her own, with your help of course. She and I have come to an arrangement. I’m to pay more rent and you’re to please me.”

“What?!” exclaimed the blushing James.

“Ah, I’d never cause such bother to a normal boy, but you’re as queer as can be. It’s written all over your face, the way you look at me is a dead giveaway. Nothing wrong with that at all. I’m a fine specimen of a man and you’re a queer, it’s only natural. Your mother knows what you are, mothers always know. Why else would she accept my proposal and send you up to me?”

“I got to go.”

“Sit right back down. You’re just nervous that’s all. You never been with a man before have you?”

“No.”

“It’s time for you to give it up. Nothing to worry about. I’ll be as gentle as possible as it’s your first time. That you’re a virgin and I’m to be your first man, that makes me even more excited, see. After a hard day’s work, a man needs relief. Now reach over and take my cock out.”

James was flushed and dizzy yet overcome with desire and excitement. He had looked at Mr. Parker. He’d hoped that his lust wasn’t obvious, but it was. James reached his trembling hand to Mr. Parker’s straining crotch, undid the buttons and out popped Mr. Parker’s big beautiful hard cock.

“That’s it. Now touch it like you touch your own. Like you touch yourself in the shed.” James peeled Mr. Parker’s foreskin and felt the wetness of the tip and began stroking it. “Very nice, now take out my balls.” James reached in and now was fondling Mr. Parker’s hairy sack in his other hand. James thought he might faint as the sensations of feeling a strong man’s cock and balls for the first time was overwhelming.

“Get down on your knees and look up close at what a man’s cock is like.” James did as he was told, and his face and eyes were now staring at Pat’s stunning manhood.

“Boy, you shall learn the most important thing that there is to do as one of your kind, how to give a man the greatest pleasure that there is. Open your mouth.” James crouched on his knees and slowly opened his mouth. “Take it in.” James was shocked yet thrilled by having a cock in mouth for the first time. “Remember what it was like as a kid to lick a lollipop and do that to my cock with your tongue. Always be aware of your teeth, no man wants to get nicked when he’s getting his cock sucked.”

James awkwardly did as he was told, and his tongue was gliding all over Mr. Parker’s shaft. The taste of male flesh was strange, yet so appealing, as was Mr. Parker’s sweaty scent. “Really do the knob and under it…” James could taste Mr. Parker’s salty discharge which excited him. “Now, get to work on my balls…Good boy…” James was slobbering on Mr. Parkers large heavy hairy ball sack.

“I must be pleasing Mr. Parker,” thought James as he felt Mr. Parker’s organ swell in his mouth from his attentions, causing him to choke and gag as Mr. Parker pushed it further down his throat. “Why was this supposed to be shameful and something to go to hell for?” James thought, not that he’d been to a church in years as his mother didn’t believe in all that. Sucking a cock felt so good and James himself was harder then he’d ever been.

“Very good! You’ve some more to learn, but you’re off to a great start, you’ll have fellas lining up for your mouth. Queers make the best cocksuckers. Women’s mouths are too small and unless they’re whores, most won’t do it. Now, stand and pull down your trousers.” James did so.” “Ah, as I thought, you’re quite enjoying yourself” said Mr. Parker, noticing James’ hard cock in his underwear. “Turn around and take down your drawers.” James was now standing with his creamy, pale and tender virgin ass on display. “Lovely.”

“AHHH!” James wailed in shock, he’d never really imagined such a thing. Mr. Parker had opened the nearby jar of Vaseline, stuck his finger in and then stuck his greased up finger into James’ asshole. James felt his insides pleasurably contracting around Mr. Parker finger as he pushed it in and out of him while twisting it around. James’ breathing became heavy and his cock grew harder.

“You’re good and loose. Get on the bed on your stomach” said Mr. Parker. James noticed there was a towel on the bedspread. Mr. Parker took his belt and folded it. “Bite down on this, we don’t want to disturb those two biddies with your howling.” James was now grinding his teeth on the belt. Mr. Parker lifted James by his hips and his ass was now raised.

“He’s going to do it to me with his cock!” thought James as he felt Mr. Parker slathering his asshole with Vaseline. “You do whatever he tells you to do. He’s a good man.” James thought of his mother’s words.

Sure enough, that’s what Mr. Parker was going to do! “You took a finger, and you liked it. You’ll take my cock, and you’ll like that even more” said Parker as James felt the greased-up knob of Mr. Parker’s cock against his asshole. James bit down on the belt as hard as he could as he felt Parker cock slowly enter and make it’s way inside him. The pain was intense as were the feelings of his inner regions spreading around Mr. Parker’s cock. James’ agonized yelling was muffled by biting on that belt, but his tears were plentiful.

Soon, Mr. Parker got his whole cock up into James and it snapped into place. There was a pause as James felt it in him. It was a moment of clarity for James. “Yes, now I know this is what I want. Sucking a cock and taking it up the ass is what it means to be a fairy and a queer and that’s what I am.” Such thoughts were interrupted as James felt Mr. Parker withdrawing his cock up to the knob and then rapidly thrusting it back in. This was repeated over and over as James now got used to this action and welcomed each thrust as he bucked his ass toward  Mr. Parker’s cock. Then there was the sensation and the sound of Mr. Parker’s balls slapping against his ass.

It seemed like an eternity to James as he was ravaged. His cock grew harder and harder with each thrust of Mr. Parker’s cock. Then there was the familiar joy of feeling himself shoot off. What a miracle! This happened without touching himself! Mr. Parker hammered away, and then James felt the odd hot gusts of Mr. Parker’s seed filling his insides up as he sighed. Mr. Parker’s cock was pulled of James’ chute and he felt wet, sore and empty in there.

“Aye, you’re a real queer now, and you’re a fine one” grinned Mr. Parker as he patted the blushing James’ head. “Boy, I’ve properly broken you in, fucked you good at both ends. You’ll follow your nature, being on your knees and bending over” said Mr. Parker as he handed James a towel. “Clean yourself up.” James wiped his soiled ass and put his underwear and pants back on.

“Have a good night, and I’ll see you again tomorrow after dinner” said Mr. Parker as he gave James a two-dollar bill.

Note: In 1934, one-dollar was the equivalent of nineteen-dollars today.