(gay prostitution, age difference, gay interracial, tough times, street rent-boys, car sex, fake cops, gay anal, rough gay sex, historical)
[There is no under-18 sex activity in this story.]
Jimmy grimaced and let out a gasp as the cock bulb breached his sphincter and the rest of the cock followed it up into his channel. He looked over at the wad of bills—four twenties and a five—laying beside the tube of lube on the seat of the wooden, straight-backed chair pulled up next to the hotel bed. To avoid as much as possible the filling and stretching sensation, and the almost immediate friction from the stroking of the cock inside him, the eighteen-year-old looked beyond the chair, across the bare wooden floor to the only window in the room, draped with flimsy, "just pretend" gauzy curtains. Dusk was creeping in on the D.C. street below, the sound of traffic was decreasing for the evening escape out to the suburbs, and a blue neon light was flickering somewhere, the hint of blue filtering into the room.
He was on all fours, his lithe chest plastered to the dingy sheet and his hands grasping the brass rungs of the headboard over his head. The john, an old, gray-haired and stubbly bearded tall, thin, sinewy-muscled geezer, was covering him from above, crouched down on his bare feet, using the feet as leverage to rise and fall on Jimmy's buttocks. It had taken the man an age to get inside the diminutive Jimmy and, now in, the john was getting the most he could out of the fuck he was paying for.
The john's cock was bigger than Jimmy had assessed it would be when the old man picked him up on the street outside the fleabag hotel. The hotel was located four blocks off DuPont Circle in an area of the city that had been blighted by the race riots that had followed the assassination of Martin Luther King earlier that spring in 1968. The man was strong, holding Jimmy securely in place under him. He probably was twice the size of the small teen. He hadn't asked Jimmy how old he was when he'd picked him up. He obviously didn't want to know—he was going for the young look and small stature—and the pretty face and the blond, straight hair that tumbled down to Jimmy's shoulders when the man had undressed him and pulled the ponytail out of the rubber band.
Jimmy had used his young, angelic looks to his advantage in the few days he'd been on the street. He found plenty of men who came to this section of town to cruise who were looking for just that.
The man had cupped Jimmy's face when he'd let the boy's hair down and gave him a tender kiss, a tenderness that the man subsequently periodically displayed and, at other times, did not. The care the man took in releasing the boy's hair told Jimmy that the man would take his time; this would not be a quick fuck and a good-bye.
It had been nearly 6:00 p.m. when the man approached Jimmy on the street, right outside this hotel, and asked Jimmy what the young man would do for him and for how much. Jimmy had asked for a hundred because the man had refused to limit it to a blow job and even to only once.
"I'll pay you eighty for the night, doing you as much as I want. I'll pay for the hotel and feed you dinner before I fuck you. You won't have to leave until checkout tomorrow."
A hotel for the night. A meal and night in a bed. How great is that? The old guy didn't look that he could hardly do one. Jimmy thought he'd probably get his rocks off and leave within an hour, giving Jimmy a whole night in a hotel bed, alone. Often at this age, they just wanted to cuddle. Truth be known, that's what Jimmy would like most too—attention and affection. God knows he hadn't gotten enough of that at home. Affection, at least. He'd gotten more attention than he could handle. That had helped put him on the street.
"A hamburger at the White Castle?" he asked.
"Sure, if you want."
"There's a good hotel near there. Won't ask questions."
"But you'd be able to produce an ID claiming you were eighteen, wouldn't you?"
"Sure, I would. I really am eighteen."
"There's a hotel right here."
"This is a fleabag."
"I'm paying for your ass, not for room service."
Jimmy knew then that the guy was comfortable with this—that he knew what he wanted and what it was worth to him. Still, he had looked like an old, gaunt geezer, and this hot and cold in switching from matter-of-fact transaction and something more tender was disconcerting. Who would have known he hung low and had the stamina and jism for three fucks or that across those three fucks Jimmy could be made to feel both treasured and a whore to be used and discarded?
He wasn't so bad, though, and Jimmy got what he wanted from it. It wasn't just the money. Jimmy loved having a man's cock inside him, knowing that the man wanted him so bad that he'd pay for it and he'd get hard for Jimmy and he'd hold Jimmy close and maybe even show him affection while his cock was trying to tear up the young man's guts. Jimmy hadn't gotten much attention or affection in life. And this guy showed him some respect and affection. He'd even plunked an extra five dollars down on the chair.
"For breakfast tomorrow. You look like you could use more in your diet."
Yeah Jimmy was small and slim but give him time. He was only eighteen. His older brother, now in the army, hadn't begun to shoot up until after he was eighteen. And his guess was that the old geezer had picked him out of the line because he was small and slim hipped—and pretty. Innocent and vulnerable looking. The man was looking for something in particular, someone to really dominate.
The man had confirmed this when Jimmy went down on all fours under the john, and the man, already with a sinewy arm wrapped around Jimmy's belly, holding him securely in place, had brushed Jimmy's hair from the side of the young man's head on the right and planted a kiss in the hollow of Jimmy's neck. He'd let the hand glide down Jimmy's side and had stroked him with a light touch of his fingers along Jimmy's flank.
"So small and sweet," he murmured. "Such slim hips. Shall we see if you can take me?" By now, Jimmy wasn't all that sure he could. Who would have known the guy was horse hung?