Chapter 9
This was crazy, Ali told herself, looking up from the couch at Curds Greenberg. He's too old, too distinguished-looking, too stuck-up to ever go for this!
Over the past week Ali had called all the men she would normally "babysit" for, informing them that, if they still wanted her for a babysitter, her regular rates applied. But, if they wanted a little attention for themselves, that was going to cost them extra.
She had done it on a dare to herself. To her surprise, all the men had agreed, and some had even told her they could probably get her a few more "clients" if she wanted. She had said she would take on new clients. But only men who were discreet and could be trusted to keep quiet about what was going on.
Curtis Greenberg had been one of those referrals. He had called her earlier that evening and invited her to spend a few hours with him. When she had agreed, he had even sent a car and driver for her, with champagne on ice for her in the back of the long black limo.
Now she was sitting on Curtis' sofa in his very expensive house, wondering if she had done the right thing by taking him up on his offer. To her, he didn't look as if he would even be able to get a hard-on.
He was very tall, expensively dressed, and the gray at his temples made him appear very dignified to Ali.
As the two sat silently across from one another, each waiting for the other to speak, Ali could see that Curtis was nervous. But so was she for that matter. She had become a professional call girl, a hooker, and she was still having bouts with her conscience about it. Since she loved to fuck and suck so much, she had told herself, and since men were willing to pay her for it, why not make some money at what she loved the most. That also meant taking on men like Curtis, who were obviously nervous about this, and didn't know where to start, which meant she would have to take control of the situation.
"What type of work do you do?" Ali asked, looking around at the rich furnishings in the house, knowing he had to be a man of great wealth to afford all this.
"I own the bank downtown, and some other real estate around the city," he replied softly, almost as if he was apologizing for it.
"Do you think I'm pretty?" Ali asked boldly, leaning back in her chair, letting her tits jut forward just a little.
"Of course," Curtis replied. "You're a gorgeous child, my dear."
Ali frowned and pushed her tits out a little more against the material of her dress. The material was thin, and she knew Mr. Greenberg could see her pink nipples through it.
"Mr. Greenburg, Curtis," Ali corrected, "I was hoping you might think of me as more than a child." She saw the way his eyes went to her tits for a moment. "I mean, a child doesn't look the way I do; or do the things I can do."
Curtis laughed and raised his glass in salute to her. "You're right, Ali. You definitely are not a child. Even a blind man could tell that. It's just that at my age, well, all young women are children to me, I guess."
Ali got up from her chair and slowly undid her dress, watching Curtis as he watched her strip. She took her time, teasing him before finally letting the dress fall to her feet. Standing before him in just a very brief pair of silk panties, garters and hose, her eyes darted down to his pants. She saw the bulge growing there, which pleased her.
She crossed the room and knelt in front of him, placing herself between his legs. She began to slowly unbuckle his belt and pants, pulling his zipper down at last. Once she had his pants completely open, she took hold of them and pulled them down, slipping them off his legs. She was surprised, but pleased, to find he wasn't wearing any underwear.
Ali was also pleased to discover he had a nice-sized cock which was rock-hard and standing straight up. She dipped her head and began to lick around the shaft of his cock, working her way down to his balls, which she sucked into her mouth one at a time. Rolling them around inside the warm cavern between her lips, she licked them thoroughly before releasing them, and began working her way slowly up the length of his cock.
She raised her head and flicked out her tongue, beginning to tease his cockhead with short licks all over its length. She took his cock in her right hand and pulled it away from his stomach so that she could lick the upper portion of the shaft. She worked her way down and around it before finally working her way back to the cockhead.
She made an oval with her lips and let the helmet of his cock slip past it, into her mouth. She sucked gently, using her tongue to bathe it with her spittle, and then gradually began to suck more and more of its length into her mouth. She took her time and went tantalizingly slow, knowing from the sounds that Curtis was making he loved what she was doing to him.
She felt his cockhead touch the entrance to her throat, and she swallowed a few times, allowing the muscles to relax. Then she dropped her head even lower, taking all of him at last.
With her nose buried in his stiff pubic hair, and her lips locked tightly around the base of his cock, Ali swallowed again, knowing that men loved it when her throat muscles massaged their spongy cockheads and hard shafts. A low moan from Curtis told her that he was no different from other men.
She began to work her head up and down his cock, using her tongue, lips, and even her teeth to stimulate him. She could feel her own juices starting to flow from the cock-sucking she was giving Curtis, but knew she wanted to please him first. At his age, his first cum wouldn't take long. But it would allow him to last longer when he got hard for the second time. And that's what she was looking forward to. She wanted him to fuck her, but she didn't want it to be over almost before it started.
Curtis growled, twining the long black tresses of her hair in one fist as he bucked his hips upward, shoving his cock deep in her throat. She grabbed his balls and squeezed gently and was rewarded with a hot blast of cum.
She swallowed it quickly, working her mouth back up the shaft of his cock to lock behind the flared head. Sucking powerfully she drew all the cum out of him. He shot two more quick blasts into her mouth, then sagged back on the couch, panting and breathing heavily.
Ali held his cock in her mouth a little while longer, making sure she had all of his cum, but finally released it when it went soft. She licked her lips and sat on the couch beside him, pleased with herself.
Curtis opened his eyes and smiled at her. "Young lady, it has been years since anyone did that for me. I can't remember it ever being that good."
"Thank you," Ali replied sweetly. "But I hope we aren't done for the evening."
"What do you mean?"
Ali snuggled up closer to him, reaching down to gently fondle his still-limp cock. "I mean, Curtis," she said softly, "that I hope you are going to get hard again and fuck me."
She took his hand and placed it between her thighs so he could feel the heat and dampness from her cunt. "I love sucking cocks, but I love getting fucked by them even more," she whispered softly. "And I just love to have my pussy sucked."
As she spoke she had gently squeezed his cock and could feel it starting to stir somewhat in her hand. She really was hot and horny and wanted to get fucked, but was afraid the older man might not be able to get it up again. Which would only leave her frustrated, and that was something she no longer believed in.
Curtis stood up and removed the rest of his clothes, extending his hand to her. "Come with me," he said softly, a glimmer in his eyes.
Ali took his hand and stood up, letting him lead her up the stairs and down a long carpeted hallway. He stopped for a moment before an ornately carved wooden door, then opened it and ushered her in. Ali looked around the room and began to feel slightly uncomfortable.
"This is my little play room, my dear," Curtis told her softly, a new firmness to his voice.
Ali looked at the room, her heart beating faster. In the center of the room was a huge bed, with heavy wooden posts at the corners, and each of them was fitted with stainless steel bolts connected to lightweight steel rings. The chains ended in the center of the bed and were attached to red velvet manacles.
"Would you like to find out what I do in my play room, Ali?" Curtis asked her at last. "Would you like to do some experimenting?"
"Why, Mr. Greenberg, whatever do you mean?" Ali asked, realizing at once this old man wouldn't really hurt her. He was just playing a game. A sexual game.
Curtis smiled and gently nudged Ali farther into the room. "I'll be happy to show you, my dear," he told her softly, the hunger growing in his eyes. "You don't know what the chains and manacles are for. But you do know what to do with this, don't you?"
Ali looked down and saw that his cock had become hard as a rock once again. She could feel her cunt begin to leak with her juices and had to lick her dry lips. The bed, with its chains, alarmed her a little. But it also excited her. As long as he didn't get rough with her, she had a feeling she was going to enjoy this fucking.
Curtis stepped between her and the bed, placing his hands on her shoulders, gently pushing her down to her knees. "Come on, Ali, suck my cock some more. Make it harder so I can fuck you with it. That is what you want me to do, isn't it?"
"Yes," Ali whispered as she dropped to her knees in front of the older man. Reaching out, she gripped his cock with both hands and guided it toward her hungry mouth.
Curtis took her head in both hands and began to fuck his cock in and out of her mouth, forcing it all the way in each time, which Ali didn't mind at all. She loved the feeling of being dominated by him, and allowed him to fuck his cock in and out of her mouth as she sucked it as hard as she could.
Ali's tits were starting to ache. Wanting some attention, she brought her hands up and played with her own nipples, while Curtis continued to fuck her mouth. She was starting to think she might actually get off this way, when Curtis pulled his cock from her mouth and pulled her to her feet. He directed her gently toward the bed.
With Ali's consent, Curtis had placed her on the bed, on her hands and knees, and fastened the manacles to her wrists and ankles. He placed two large pillows beneath her waist, forcing her into a doggie-style position-which Ali didn't mind in the least. She loved getting fucked in any position. But this was one of her favorites.
Curtis pushed her head down on the bed and knelt behind her. Spreading her legs wide, he began to lick the insides of her firm thighs, gradually working his way to her steaming cunt. The minute his tongue stabbed in between the widespread, swollen cunt lips. Ali arched her back and began to cum.
"Ohhhhh, this is so weird!" she cried as Curtis began to attack her pussy in earnest.
She was manacled to the bed and couldn't really move; not that she wanted to, as Curtis was sucking her cunt excellently. But the whole experience was strange.
Ali wailed and jerked her ass around, looking up to see her reflection in the mirrored door of Curtis' closet. She had to admit to herself, she did look sexy as hell amid the gleaming chain links, her long raven hair hanging down, her full tits shaking, her cute ass perched up in the air, with Curtis' face buried in her cunt.
Ali was not frightened in the least. She was finding herself getting extremely turned on by this. She could feel her cunt flowing freely and her nipples hardening even more. She rubbed them against the silk sheets of the bed, loving the feel of the material across the hard nubs.
"I see you like my little games, don't you?" Curtis growled, as if reading her mind.
"Yes! Oh, yes! I love it!" Ali replied, trying to push her ass back, hoping that Curtis would get back to sucking her cunt. Or, better yet, fuck her.
Curtis grabbed the firm cheeks of her ass, spread them apart and lowered his head again, beginning to lick all around her ass. A strange, hot feeling swept over Ali as the cool air washed over her spit-slicked ass. And she nearly jerked free of the chains when Curtis snaked the tip of his tongue into the tight pucker of her ass. The wet, slick tongue forced the ring of taut ass muscles open and worked its way inside.
"Ohhhhh, fuck! What are you doing?" Ali screamed. A totally new sensation shot all through her body.
Curtis paid no attention to her cries. He continued to wet her ass with his spit, and sink his tongue in her anus as far as he could.
"Eehhgg! Oh, sweet man, that feels fantastic!" Ali whimpered as Curtis began tongue-fucking her clenched asshole.
The super-tight passage slowly began to loosen. Ali was moaning, a soft, throaty cooing that let him know she loved what he was doing to her, very, very much.
A long sigh escaped her lips when the invading tongue slowly slid from her ass at last. "That was so nice!" the raven-haired slut said with a sigh. "I ... I wish you would do it some more!"
Ali felt like a real pervert, asking for more of that odd, thrilling, exciting tongue-fucking. But she couldn't help herself. It had felt so wonderful, in the strangest son of way, and Ali wanted more of it!
"Oh, there are even nicer things in store for you tonight, my dear," Curtis assured Ali as he raised up on his knees behind her. His long, hard cock was bobbing just behind her pussy slit. "I can promise you that."
Ali watched their reflection in the mirror and saw Curtis easing his cock toward her cunt. She felt the heat of his enlarged cockhead nudging apart her wet pussy lips. He pushed forward and eased his cock into her cunt, drilling it all the way in with a single plunge.
"Ohh, yes!" Ali shivered. "Fuck me! God, I need it! I need to be fucked and fucked and fucked!"
Curtis obliged her by fucking his cock in and out of her clutching cunt, causing Ali to groan with joy and pleasure. He fucked her tight cunt-sheath until his cock was gleaming with her slippery juices. Then suddenly he withdrew it from Ali's clinging pink folds just as she was about to cum.
"Wham NO, WAIT! Put it back!" Ali howled. "Put it back and fuck me, please! I want it! I need to be fucked!"
"And you shall be fucked, my little beauty," Curtis chuckled softly from behind her. "But, perhaps not in the way you expected."
Ali tried to focus her lust-glazed eyes on the mirror, and for a moment she didn't understand what Curtis meant. But her eyes widened as she saw him lining up his bloated cockhead with the cheeks of her ass, rubbing it all around her asshole to coat it with her slimy juices.
"Wait! What are you going to do?" she asked as Curtis began to exert a steady pressure with his cock against the tightly puckered ring of her ass. "Curtis, I've never been fucked in the ass before! I'm not sure. Fuck my pussy, please. Just fuck my pussy!"
"Just relax, Ali," Curtis panted. "If you relax, you'll enjoy this, I assure you."
Ali let out a little gasp of surprise as the head of Curtis' cock slipped past the tightly clenched ring of muscles, realizing that it actually didn't hurt at all. It was a bit uncomfortable. But there was no real pain involved with it. She concentrated on forcing her ass to relax, and felt more of his cock slide into her.
Curtis was going to fuck her ass, she might as well enjoy it and get as much pleasure from it as she could.
Ali tried to do what he said, to get her ass to relax more. Slowly she felt the tight sleeve of her ass open like the petals of a flower. She felt Curtis push more and more of his steely prick into her virgin anus, and she moaned as the hot inches of prick pierced her. But she kept her ass loose until she finally felt his pubic hairs grinding against the smooth cheeks of her rump. And Ali knew she had taken all of him at last.
"So hot. So velvety hot!" Ali heard Curtis moan from behind her. She could feel his cock jerk and twitch slightly deep within her bowels. "Nothing like a virgin ass!"
"Um, Ohh! Ohmigod!" Ali whined as the fat hunk of cockmeat pulled back part way, then slipped forward into her sucking chute.
It felt so strange to have a long, slick cock being thrust up her ass! It was hot, throbbing, and very exciting to her; she found it was turning her on.
"Now you're taking it!" Curtis breathed hotly. His fingers were running up and down Ali's back, then they slipped around her body to her dangling tits and squeezed them. "Now you 're taking my big cock up your ass!"
The older man held onto Ali's tits as he drove his prick in and out of her ass, again and again. He pulled on her distended nipples as he fucked her, and Ali could feel a gradual change coming over her.
Her ass was aflame with desire and was starting to come alive with the strangest, most wonderful sort of throbbing pleasure she could imagine. Each stroke of the rapidly fucking prick brought a new surge of stronger, hotter sensations as it glided in and out of the lewd young woman's tight ass.
"God, I never thought that it could feel so good!" Ali moaned.
Curtis laughed and rammed his cock into her harder and faster. He squeezed Ali's pert tits, his fingers sending tiny jolts of ecstasy from the pink nipples to her tingling clit and pulsing asshole.
"Ali you young women love ass-fucking, once you do it with someone who knows what he is doing!" Curtis grinned, powering his cock into the opened asshole. "You all pretend you're so innocent, that you would never do anything like this. But once you get a cock up your ass you go crazy and love it!"
Ali wasn't about to argue with the man. Because, as far as she was concerned, what he was saying was completely true. She had never thought she could enjoy getting fucked in her ass. But right now she loved it and didn't want him to stop.
She could tell Curtis was about to dump his load right up her ass, and that turned her on even more. His prick seemed to be growing even larger inside her gripping ass sheath. His breath was starting to expel in ragged gasps while he massaged her titties hard and rammed his cock into her.
"Cream me, Curtis!" Ali moaned to the rutting man. Exotic unreal feelings were rolling through her hotly-fucked ass. "Fill my ass with your cum!"
"Ohhh, I'll cream you all right!" Curtis panted. "I'll fill your pretty young ass, you can bet on that!"
The hunched-over man hammered his thick cock into Ali's gripping ass harder, deeper, faster. The wild friction of his prick reaming her ass sent fresh waves of fiery sensations through her ready-to-climax young body. She bucked her ass backwards in time with his thrusting fucking motions.
"Oohh, fuck me! Fuck my hot ass!" Ali screamed, nearly delirious with the incredible feelings pounding through her.
Curtis gasped as the young woman's clenching ass began squeezing and caressing his thrusting prick like a million feathery fingertips. He slammed his cock as deeply into her as he could, arching his back as his balls released their load into her bowels.
Ali clamped down on his cock with the muscles of her ass, loving the feeling of fullness it made her experience when her own climax erupted within her.
"Milk it, you hot young slut!" Curtis yelled as he tried forcing more of his cock into her.
Ali mewled and whimpered as the furious ass-cum tore through her body. Her asshole spasmed wildly around the impaling cock, the clenching twitches spreading quickly to her untouched cunt and up to her well-mauled tits. The full mounds of her fleshy breasts heaved and fluttered as if they were possessed of a life of their own.
"OHHHHHHH GODDDDDD!" Ali screamed. She threw back her head as the torrid spasms engulfed her completely.
Curtis' prick bucked inside her churning ass. Ali felt-through the furious climax engulfing her- the first hot wads of cum splashing into her ass. The white hot jism jetted into her tight ass and seemed to flood it completely.
"FUCK MY ASS!" Ali pleaded wildly. "Oh, Dear God, FUCK MY ASS!"
She heard Curtis groan and felt him ram his cock in and out of her quivering ass, the spurting cock gliding quickly and easily in its own coating of wetness.
"Yesss!" Ali screamed, cumming even harder when she felt the heat of Curtis' prick knifing into her again and again.
"Oh, Ali, Ali, Ali...." Curtis cried out. "Your ass is the tightest, the sweetest, the hottest that I've ever fucked in my life!"
The man kept pounding his cock into Ali's ass until he had no more cum to shoot. He finally pulled his rapidly deflating prick gingerly from her tender ass, and collapsed on the bed next to her.
"Oh, what a fuck you are, my dear!" Curtis told her weakly. "What a gorgeous, glorious, beautiful fuck you turned out to be! Who would have suspected by merely looking at you? You look so young, so pretty. And so, seemingly, innocent."
Curtis patted Ali's ass appreciatively and began to loosen her leg and arm restraints. Ali collapsed on the bed in exhaustion and Curtis took her in his aims and held her gently, caressing her softly.
"That was just absolutely fantastic!" Ali told him, her voice a soft whisper. "I've never been fucked in my ass before and I wasn't sure I would like it. But it didn't really hurt, or anything. And ... well ... it was fantastic. Thank you."
"For what?" Curtis asked.
"For showing me something new."
"Well, you're certainly welcome. I just hope we can get together again sometime."
"Of course. You know how to get in touch with me, and you know my rates." She felt slightly uncomfortable about bringing up the subject of money.
"Why don't you get cleaned up, my dear," Curtis told her, pointing to the door at one side of the room, which she guessed was a bathroom. "I'll meet you downstairs and we can finish up our little arrangement."
A few minutes later Ali was back in the limo being taken home, two crisp one-hundred-dollar bills in her small clutch purse, and a smile of satisfaction on her beautiful face.
"I could get to enjoy this type of life," she said to herself as the limo driver dropped her off in front of her house.