When Bill got to Penn Station in New York, he was a little disappointed to find it almost deserted.
When he hit the street, the story was the same. He expected to see a bunch of whores banging around waiting for him, but be knew that was ridiculous. He would have to go to the right part of town or know some phone numbers.
He'd always heard that Times Square was a good place to find whores, so he headed in that direction after stashing his bag in a locket. It was exciting to be back in the city after his exile at school, and he felt more confident that he was going to get fucked than he ever had before.
As he neared Times Square the crowd began to thicken. The lights were blazing on the signs and marquees. He stopped at Broadway and looked around. There didn't seem to be any whores standing around; everybody seemed to be in motion, flowing along the sidewalk.
Then a voice filtered through the sounds of the street.
"Want a girl friend? Hey, sport, looking for a chick?"
Bill stopped and looked in the direction of the voice. There was a guy standing in a doorway, talking to him. The guy motioned Bill over to him. No wonder be hadn't seen any whores around, he thought. They all wed pimps to get their customers. Anybody would know that.
"Hey, you want a chick? I got a real gorgeous babe for ya, kid."
"Uh, where is she?" Bill asked. He didn't want to seem dumb, but it seemed to be a good question.
"She's waitin' for ya, man. Come on. I'll take ya there."
"Uh, what's she look like?" Bill asked.
"She's dynamite. And if she don't look good enough, there's six other chicks all available."
Bill walked beside the guy and was led into a doorway. He found himself in the shabby lobby of a hotel. There was some torn up furniture and a desk without anyone behind it. It looked shady, but what could you expect, Bill figured.
"Gimme twenty and she's all yours," the pimp said.
Something seemed fishy to Bill. The guy saw him hesitate, and asked him what was the matter.
"Well, where is she?" Bill asked again.
"Room six-eleven," the pimp said. "She's waiting for ya. She'll do anything ya want. Suck ya, fuck ya, she can do both at the same time. Come on, man. I ain't got all night. Twenty, and she's yours."
It still seemed fishy to Bill, but he'd come this far. He wanted to get fucked so bad that he would hate himself if he blew it now. He took out his wallet and pulled out a crisp twenty-dollar bill.
The pimp took the bill and said, "Have fun, sport." He slapped Bill on the shoulder with a smile, and left. Bill was suddenly left alone.
Looking around he saw an elevator door and went over to it. Then be noticed a guy behind the desk, leaning back in a chair and snoozing. Bill cleared his throat to get the guy's attention. When the guy opened one eye to look at him, Bill told him to take him to the sixth floor.
The guy got up slowly and came to the elevator. Bill saw how old and stooped the guy looked as he led him into the elevator and turned the crank that made the door close, and the elevator began to rise. When they got to the sixth floor the door opened, but the elevator was about a foot too high, arid the old guy had to jerk the handle back and forth to get the cage even with the floor. Bill stepped out and was left alone once again. The hallway had gray and leprous walls. He felt a panic when he tried to remember the room number. Then he was sure that the pimp said six-eleven. Yes, that was it.
He walked down the hall until he found the room. He straightened out his hair and clothes, and, with a lump in his throat and one forming in pants, he knocked. He hoped the girl was as good as that pimp said she was. Nothing happened. Bill knocked again, louder. Still nothing. There was no doubt that he had the right room. He began to think something was wrong. But he knocked again, this time as hard as he could.
A grunt came from the room, but Bill couldn't tell what it was supposed to mean. Now he was getting mad. He banged on the door again.
"All right, all right," he heard a voice grumble on the other side of the door. It didn't sound like the voice of young, sexy chick, though. The door swung open, and Bill saw an old guy standing there in a dirty robe, squinting at him.
"What do you want?" the old guy asked.
Bill didn't know what to say. He was confused and aggravated that things weren't going well.
"I'm looking for a girl," he said. "Uh, she's supposed to be, uh, waiting for me here." As he spoke, his voice became an uncertain whine.
"What?" the old guy asked incredulously. "There ain't no girl in here. Geezes, a guy can't even get a night's sleep." The voice trailed off and the door was slammed in Bill's face.
For a few seconds Bill stood there, not knowing what to do. There must be some mistake, he thought. The room number was right, though. Bill thought of knocking again, but he realized that wouldn't do him any good. Then it hit him. There was no girl. He had given his money to a perfect stranger and been sent on a wild-goose chase.
His prick shriveled and he felt like an idiot. How could he have been so stupid? He felt his horiness turn to rage as he stood there. He hit himself on the head with his fist and headed toward an exit sign. He couldn't face that guy who ran the elevator now, and he would have to take the stairs. As he ran down the dark and creaky staircase, he swore he would find that pimp and get his money back.
Bill hit the street and headed for the doorway where he'd seen that guy. On his way, he heard the same pitch about ten times. But it was never the same guy, and when he got to that doorway, it was empty.
There was nothing to do but chalk it up to the experience, but Bill was still pissed. If he was going to get fucked, he would have to use his head.
He went to the station and picked up his bag and began looking for a hotel. His anger made him forget the weight of the suitcase, and he walked fast toward a neon hotel sign. It was a place that looked a lot like the one he'd just come from, but he knew he wouldn't be able to afford a better joint.
The room cost him as much as the nonexistent whore had, and he knew he wouldn't last long in the big city with his meager finances. Now that his anger was dissipating, his horniness was returning. As he was being taken to his room in the elevator, he asked the clerk about whores.
"Yeah, I can arrange it," the man said.
Bill asked him how much it would be, and the guy said twenty bucks.
"I'll only give the money to the girl," Bill said with a tone of shrewdness.
"Well, of course, what else?" the clerk said. "But you've got to give me five now for my trouble."
Bill didn't want to give the guy the money, but be figured he could always find the guy in the lobby, and things must be on the up and up. He handed the guy a five, went into his room and waited. The room wasn't too bad, but the bed was so soft that it was more like a hammock. Bill looked out the window, but there was nothing except a brick wall about ten feet away.
It was almost two in the morning, and Bill was feeling tired, but his hard-on was keeping him buzzing. He wished he had asked the guy how long it would take for the girl to get there. As he waited he recalled peeping into that dorm window. It seemed like years ago.
When be heard a knock on his door, he jumped. Suddenly, his heart began to pound. He shook with a mixture of lust and shyness as he walked to the door. It was very suspenseful to open a door and get his first look at the chick who would relieve him of his virginity.
When he opened the door be was faced with a woman who looked pretty good. Bill stood aside and walked in. He sized her up with horny interest. Her body was a bit chunky, but she had big tits and a wide ass. Her hair was piled up on her head with swirls and waves, and her face was colorfully painted. She walked to the middle of the room and began unbuttoning her black, silky blouse.
Bill closed the door and stood still, watching her. It was hard to believe that there was a woman in his room, taking off her clothes and willing to fuck him. He just stood there and watched.
The whore took off her blouse and threw it on the chair. Her big tits were suspended in a black bra, and they overflowed, spilling out on her chest.
She shifted her weight, put her hand on her hip and said, "Want me to undress first?"
Bill nodded. He felt that he should do something, but he wasn't sure what. His cock was sure ready. He could feel the pain of its confinement in his tight pants.
The whore reached behind her, just like the girl he had peeked at through that dorm window, but somehow, the effect was different. But at least this chick was at his disposal. She threw her bra after her blouse on the chair and showed her tits to the horny, young boy. They weren't very firm tits, but Bill couldn't complain. He was eager to get his hands on them.
She unfastened her red slacks and pulled them down. As she readied down to slip them off her feet, her tits swung lewdly. Bill wanted to go over to her and caress one of those pendulous boobs, but before he could go to her, she stood up again, and her tits slapped on her chest. Now that her body was being revealed, Bill could see that it wasn't exactly all be could hope for, but he wasn't in any position to be fussy. He was getting wild with passion, and wouldn't be able to control himself much longer.
The chick pulled off her panties and stood facing him. From the front, her tits looked pretty good. They had huge, round nipples. Her waist was fairly narrow, and her cunt had a thick carpet of hair over it. Bill's eyes fastened on that bush and in a trance of lust, he walked to her.
As he got close, he could smell her warm body. It was a combination of pussy odor and cheap perfume, but it had a strong influence on the needy kid. His hands jerked up to her tits and he grabbed one in each hand. He stared at them as he kneaded flabby flesh.
As he played with her tits, the whore unbuttoned his shirt. She helped him off with it, then went to work on his pants. Bill stood there like a manikin, while she lowered his pants and lifted his feet out of them. His huge cock was holding the front of his underpants out like a tent, and the whore smiled at the sight of it. Bill was feeling braver, and was dying to get his prick buried in her twat.
When she pulled down his shorts his dong stood out proudly and quivered impulsively. The whore dropped to her knees in front of him and took that pounding dick in her hands. Bill was instantly filled with powerful jolts of pleasure. Her fingers caressed and toyed with his cock with such skill that he knew no chick his own age could equal it.
Bill's legs grew weak as he was overcome with passion. He had to put his hands on the girl's shoulders to support himself. She cupped his balls with one hand while she ran her fingers around the taut skin of the bloated cock-head. When she moved her lips to the tip of his prick and lightly kissed the tiny slot, Bill shook and tensed his body. His cock began to quiver in a way he'd never seen before.
The hooker stood, pushed Bill down on the bed, then crawled on beside him. Leaning over his crotch, her mouth went to work on his prick in earnest. He held his head up so he could watch her red lips open and encircle his twitching tool. When he felt the wet heat of her mouth close on his cock, be closed his eyes and collapsed on the bed.
Bill concentrated on the way she used her tongue on his cock-head. She would brush the wet surface back and forth on the bottom of the prick, then run it all around the big knob. He kept lifting his head to look, but his raging lust made him throw his head back down on the pillow. His arms were flailing the sheets and his legs jerked.
To increase the almost unbearable pleasure, the whore was slipping her hand up along the inside of his thigh and tickling the area under his balls. If Bill hadn't jerked off several times earlier that night be would be filling her mouth with jism now, but as it was, be was building slowly to a towering climax.
She really knew how to give head, Bill began to realize, as he felt his orgasm sneak up on him, then slide away as she cased her tonguing. She had brought Bill to the verge, and was keeping him there with her consociate skill.
Through his delirious pleasure, Bill decided that he wanted to come in this whore's cunt rather than in her mouth. After all, he wanted to lose his virginity and he wasn't sure if it would count to get only a blow-job.
He clutched at her head and tried to pull her off him.
"I-I-I want t-t-to f-f-f…" he managed.
She slipped her lips from around his cock and flopped down next to him. Bill frantically scrambled up and got between her legs. He thrust his hips, and his prick stabbed at her pussy, but the first lunge missed. He felt his prick bounce off her plump mound, drag through some coarse hair and slide up her belly.
He tried again, but the same thing happened. His juices were already beginning to surge, and he only had a few seconds before he would overflow with ecstasy and cream. In his desperation, be began making wild pokes at her crotch, but he wasn't hitting her cunt. The whore tried to help by grabbing his plunging prick and pulling it to her hole, but that only had the effect of holding his loose skin while Bill pulled and pushed his bone, and it made him come even sooner.
When Bill felt his prick burn with the joy of coming, be stabbed it into her crotch and rubbed it on whatever be could. His jism began covering her thighs and muff as his prick bounced around in the general area of her cunt. His hips pumped madly and he was engulfed in bliss even though be was off target. The whore squeezed her heavy thighs around his cock and that felt good. He stopped shooting finally, and rested on the comfort of her chubby body.
Bill wanted to rest a while, but the woman wiggled out from under him. She got off the bed, mopped up the spilled cream and began getting dressed.
"DO you have to go already?" he asked. "I thought we could try again."
"Do you want to go again?" She smiled at him and her eyebrows shot up. Then she looked serious, and said, "It'll cost you another twenty."
Bill thought about it for a minute, them told her to forget it. He thought he'd be better off waiting until he was sure he could have a great orgasm. He was running out of jism and money. He watched her finish dressing and waddle out of the room.
He wasn't sure if he was still a virgin or not, but he suspected that he was. It didn't matter, because he was still determined to get fucked properly as soon as he could. He promised himself that the very next day he would try again, and be more careful. Still, be did have fun. The whore was all right and he had broken new ground. He felt that a new life was beginning for him.
Bill fell asleep thinking about the near fucking he'd gotten, but in his dreams be did better, and the old whore was transformed into a gorgeous, voluptuous chick who looked very much like his mother.