James Grady

Edmund Collins III would call James a few days in advance to make an appointment. Since their initial assignation which had been instigated by his son, Mr. Collins had enjoyed James’ services several times over the ensuing months. Dressed in a suit and tie, James would take the subway from Brooklyn to Manhattan and would arrive at Mr. Collins’ suite at the Waldorf.

Weary from board meetings, worn out by managing one of America’s greatest fortunes and taken up with family and social obligations, Mr. Collins looked forward to the pleasure of undoing his red silk dressing gown, laying back on a wingchair and having James suck his cock and then fucking James' ass. Mr. Collins who’d enjoyed boy whores around the world had never met one who so enchanted him as James did.

Without his son around and for whom he felt compelled to put on a display of exaggerated brazen masculinity he could savor fucking James in bed on his back with legs spread and lifted high up. He even bent his head down to kiss James as James not only totally surrendered to Mr. Collins’ cock but also to his being. James knew and ardently accepted his place in the world by giving over his mouth, ass and presence to those above him. Of course, that he received a fifty-dollar bill for his afternoon of subjugation was a great incentive but they both knew there was more to it. There was the mutual lust between men charged with the acceptance of who had power.

After they’d fucked and shot off, there were luxurious hot baths in the Waldorf’s grand bathroom. Then in their silk dressing gowns they smoked  cigars and sipped brandy. This ritual would be followed by a fine lunch wheeled in by a uniformed handsome waiter.

Mr. Collins who routinely dealt with employees, toadies and sycophants, enjoyed conversing with James, an earthy young man from the streets who read newspapers and could keep up his end of the conversation. Mr. Collins even gave James financial counsel. He had his attorney draw up incorporation papers for James’ bakery that allowed him to launder his bounty of cash from his whoring so that it could be legally invested and grow, rather than laying hidden in cigar boxes.

“I’m certainly interested in your proposal and accept the conditions. I look forward to providing satisfaction” replied James after Mr. Collins had outlined an upcoming event. So, a month later on a Saturday evening James was at Mr. Collins’ Waldorf suite.  

Justice Jeffries, Senator Benson, Gov. Bracken, and Chief Executive Officer of Galaxy Pictures Mr. Holloway were gathered in the drawing room of Mr. Collin’s suite, smoking cigars and drinking. There was joviality at this annual reunion of these Yale graduates. They were like Mr. Collins all 43 years old, in excellent physical condition and handsome. Once a year they gathered in New York City for a game of poker and camaraderie as they all had become close at Yale. Being men of the world, such a meeting included carnality.

The procedure was that while four men played poker, the fifth would visit James in a bedroom to be pleasured. James was nude except for a white undergarment with hole slit in the ass area. He was excited and his hard dick and his balls made a noticeable bulge in the undergarment.

Burly bearded Gov. Bracken (Republican of Michigan) was the first to arrive. He undid his trousers and sat on a wingchair. He puffed on a cigar and sipped whiskey as James sucked his large fiery uncut cock. James did the governor nice and slow, lapping his juice. The governor grunted, pulled James off his cock and stood. James rose went to the divan and positioned himself on his hands and knees. The governor stuck his hand in a large tub of Vaseline on a nearby table, greased up his cock, shoved into James’ ass and proceeded to fuck him solidly. The governor grunted, shot off in James and left. James cleaned himself up.

Tall and aggressive Senator Benson (Republican of Ohio) arrived next. He had James on his knees for a furious round of face fucking. James could barely keep up with the senator’s large uncut cock thrusting in and out of his mouth with the senator’s hands around his head, but he serviced the senator to his satisfaction. James was on the divan as the senator bluntly fucked him from behind.

So, it went with thin beady Justice Jeffries (appointed by former President Herbert Hoover) who after having James suck his large uncut cock had James ride it until he climaxed.

The exotically handsome dark-haired sensual Mr. Holloway arrived and was the most passionate of the group. He groped James’ ass and felt up his nearly nude lithe body and got James so hot. Mr. Holloway was the only one to get undressed. James was surprised to see that Mr. Holloway’s fat long cock was cut. 

“That’s quite a schlong Mr. Holloway” said James.

“Ed said you were special” laughed Mr. Holloway. “The name used to be Herschkowitz, before my father changed it. Now,  show me what you do with a schlong.”

James was invigorated by the banter and friendliness and proceeded to put his heart and soul into sucking Mr. Holloway’s cock.

“Oy gevalt! Ed wasn’t kidding at how great you are. I’ve never seen a fagaleh go down to the base like that! I could lay back forever watching you.”

Eventually, Mr. Holloway positioned James on the divan on his back legs up. He greased up his thick long cut cock and slowly penetrated James. Mr. Holloway was quite different from those pillars of society. Mr. Holloway was a cocksman who fucked with ardor. His cock hit all the right spots in James’ nether regions, James gurgled joyously as this man who truly knew how to fuck was fucking him. James howled as his cock began shooting off gobs of jism, staining the front of his undergarment which encased his cock and balls.  

“So, it was good for you too” chuckled Mr. Holloway. Soon he was groaning as his cock sputtered copious blasts of spunk in James. They cleaned up and Mr. Holloway poured them glasses of whiskey and they sat on the divan they’d just tremendously fucked on, smoking, sipping and chatting.

“Tell me about yourself” said Mr. Holloway. James give a capsule summary of his life.

“What a picture that would make! An All-American boy, his mother and his man survive hard times with pluck and humor! I don’t know if Iowa is ready for that” laughed Mr. Holloway. “Write your phone number down. I’m here for another week before I go back to Hollywood, I have a proposition for you.” James wrote his phone number down. Mr. Holloway got dressed. “I have to get back to the goyim. Still, friends are friends.” James cleaned himself up and put on a new undergarment.

“You’re the belle of the ball!” laughed Mr. Collins as James was sucking his cock. “Everyone is very pleased with you.” Mr. Collins heartily fucked James on his back on the divan, cleaned up and went back to his guests.

James took a hot bath and got dressed in his suit and tie. The party was over, Mr. Collins handed him an envelope with five 100-dollar bills.

“I also want you to have this” said Mr. Collins handing him a thin medium-sized object wrapped in brown paper. “It reminds me of you.”

“Why thank you so much, Mr. Collins” said James as kissed him on the mouth.

James rode the subway back to Brooklyn carrying his gift.

Nora, his mother and Donny were still up and greeted him. James unwrapped the package.

“Oh!” gasped Nora. “I know just the place for it” she said as they went to the living room with a hammer and nail to hang the painting.

“It looks like a weird Jimmy!” exclaimed Donny.

“Oh, go on. I daresay our living room is the only one in Brooklyn with a real Picasso in it!” said Nora.

Indeed, it was a Picasso self-portrait from 1905 capturing him in all his charismatic youthful sensuousness with a cowlick of dark hair, large haunting eyes and an alluring facial expression.