Taking It To The Streets, Chapter 5

"The weekend ends too quickly for the pair... But William has a plan!"

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Having already seen her oral skills, sampled her delicious tasting pussy and ass, and been treated to the best fuck he’d ever had, there was only one more stop on his tour of this beauty. 

“Okay now, get up on your knees and show me that big beautiful ass!” he said. “I’m going to fuck that sweet ass just like I fucked your pussy!”

“Ooh yes! I love a hard, thick cock in my ass! Yes, fuck my big whore ass baby! Fuck it deep and hard!” she squealed, scrambling to get into position. 

When she had gotten to her knees on the bed and put her face to the bed sheets again, he moved in behind her. “In my purse, there’s a small bottle of lube… it’ll make things easier,” she said. He got her purse and got the small squeeze bottle of lube out. 

“You come prepared for anything, don’t you!” he said.

“Well, you never know what kind of perverts you’ll come across in this job!” she giggled, “And I do a lot of sitting when I’m not laying down or kneeling!”

“I’m going to see to it you don’t do a lot of sitting around THIS weekend!” he said.

“Mmmm, that sounds wonderful to me, lover!” she said.

“First though, we have to make sure that tight little ass of yours is lubed up and ready for me,” he said. He popped the lid up and squeezed a generous amount of the slippery gel onto her rosebud. He spread the edges out around her sphincter and over her crinkled anus. 

Slowly he introduced the tip of his finger into her and felt how tight she was. He put another smaller amount on the hole and pushed in again, this time getting up to his first knuckle. Then he turned his finger around inside her ring, coating the whole inside with the lube.

“Ohhh, William, that feels so good! I love being fucked in the ass! Please hurry, I want to feel your big, fat cock back there! I want you to stretch my tight asshole so wide! Ohhh, God!” she moaned.

He thrust his finger a little deeper into her rectum and pumped it a few times to help spread the lube a little further into her tight hole. Then he pulled his finger out and adding a bit more lube he pushed two fingers in this time, opening her hole wider.

“Ohh yesss! Ohhh God, baby, fuck me with your fingers!” she moaned, pushing her hips back at him. When she was loose enough for his two fingers he pulled them out. 

This time he introduced the index finger of both hands back to back into her asshole. then he began pulling her asshole open stretching her wide and working around the perimeter. 

This really set Ruth off and she moaned and whimpered and groaned her delight at his efforts.

“Ohh fuck baby! Oh, you are opening me so wide! Ohhh, I can feel you…stretching me soo… Oh, fuck yes! Hurry lover, I want your cock in there! Give me that big beautiful hard cock!”

Once he thought she had been opened up enough, he pulled his fingers out of her ass. He took the lube one more time, this time putting a good glob of it in his hand. 

Rubbing it all over his hard cock, he added a small glob to her ass to give it a bit more lubrication and then moved closer to her.

Using the tip of his cock he smeared the lube around and over the little pink star. 

Ruth moaned impatiently, “Put it in my ass… hurry… fuck my asshole with your big cock… right there… that’s it… uuuhhh… oh god…oooh…”

William pressed his cock into her slowly. She was tight still but not so tight it had difficulty slipping inside her. 

His efforts at relaxing her with his rimming, along with the stretching and opening her had helped. He slid in slowly and as he sank deeper into her ass she groaned and moaned happily.

As William began to slowly move in and out of her, Ruth reached between her legs to play with her pussy and clit. 

He sank a bit deeper with each thrust forward until he was fully inside her and his hips bounced off her ass cheeks with each full thrust.

She put her hand on the wall next to the bed to brace herself and stuck her ass out with her legs spread. 

“Okay now fuck me, William! Please, I need you to fuck me hard and deep … right now… please, William. Fuck me like you hate me, please,” she cried.

William gathered himself for a full-out assault on this woman’s lovely ass. He began slamming into her hard and deep, just as she had asked, shoving his hot meat into her tight asshole and nearly bowling her over with each thrust.

Ruth rubbed her swollen clit frantically. She could feel his hard cock moving in and out of her rectum, slick with the lube and the juices from her drooling pussy as it slid in and out of her. She was on fire. She could feel a powerful pressure building in her tummy.

“Oh god yes! Fuck me, William, fuck me dammit! Your big cock feels so good… fills my ass so full. Oh god, oh god, yeesss! Ohhh fuck me!” she cried as he slammed into her over and over again.

He reached forward and grabbing a handful of her hair hauled her head upwards to a regular kneeling position. 

“I need to get to those amazing tits… so my hands have something to do too!” he said. 

He grabbed one of her massive tits with one hand and reaching up to grab her throat with the other. 

Careful not to choke her, he squeezed just hard enough for her to have to work a little to breathe. He wanted to claim ownership of her, to show his dominance without scaring her or hurting her.

“Oh God, baby, I love your cock! I love the way it fucks me, so deep in my ass. Ohh yeah… that’s it… fuck me… fuck me and make me yours, lover… harder… oooh…”

Sweat was dripping off William’s forehead, falling onto her ass and running down the crack to where his cock pistoned in and out of her. 

He was giving her all he had and she was asking for more! She might have been used to this kind of exertion but William certainly wasn’t. He needed something… something to level the playing field. 

Then he remembered her affinity to being spanked. That’s it! That’s the ticket! He brought his arm back and gave her ass a healthy swat.

SMACK!

“Ohh God!” she moaned.

SMACK!

“Ohh fuck, yes! Spank me and fuck me! Ohh!” she cried louder.

SMACK! SMACK! SMACK! SMACK! 

He gave her four swift, hard swats and she shuddered as her orgasm rose inside her.

“Oh, William, I’m going to cum baby! I’m going to cum!” she cried out as she neared her crest.

She stiffened then jerked, reaching behind her to grab anything her fingers could sink into. His cock continued to pound into her. Her orgasm seemed to go on and on. Her legs were weak and she was whimpering. 

“Please… I… can’t stand… oh god… nooohhh… aaaahhh…FUCCKKYESSS!” she screamed.

Another orgasm smashed into her, washing over her like a tidal wave and draining whatever energy she had left. He finally pulled out. Ruth slumped to the bed, completely drained. William picked her up and moved her further onto the bed and lay down next to her letting her rest. 

But he didn’t actually let her rest all that much. As she lay there recuperating and getting her wind back, he played with her tits, fingering her nipples, rolling them between his fingers and lightly pulling and plucking them to make them harder and erect. 

He took the nearest one in his mouth as his hand slid slowly down her stomach towards her pussy.

“Ohhh Goddd,” she moaned in protest to this new intrusion.

But William had his mind made up and continued on until he reached his goal. He licked and sucked on her hard nipple as his fingers played in her still wet pussy, fanning the embers of her fire and stirring them back to life. 

Ruth opened her legs wider as she reached up to hold his head to her tit. She played with her other tit herself as she got more and more aroused.

William watched her as she closed her eyes and softly moaned, her body responding even though he had already put it through more than she was used to on any regular night. And he wasn’t finished with her yet. 

He was going to make sure she earned her money and so he moved around to her feet. He spread her legs wider and started licking her with his tongue, pressing his lips against her sex. 

The fire between her legs burst into life once more, the juices flowing freely from within her. 

Ruth put her hands on the back of his head and moaned again, enjoying the pleasure his mouth and tongue was giving her as he licked the nectar from her gash, sucking and slurping with his lips clamped around her swollen mound.

Her sexual hunger soon returned, and she responded to the ministrations of his tongue and aggressively humped her pussy against his mouth. Then he heard her words.

“Ohhh fuck, William! Oh God!” she screamed out as she grabbed fistfuls of his hair and shoved his face even further into her depths.

She groaned and bucked her hips slightly. Her continuing to scream his name out only encouraged him more.

Next William slowly pushed a finger into her under his chin, massaging the inside of her walls and watching for her reaction as he searched for those favorite pleasure spots he knew she had. It was then that he noticed how flushed she was. 

Her chest, her face, all that beautiful pale skin that he had kissed and caressed just minutes before, was brushed the most attractive pink and she had a sheen of sweat to set off the glow. She looked even more beautiful.

“You look so fucking hot right now. You like what I’m doing?” he growled as she bucked against his mouth.

“Yes! Oh fuck, William! Oh my God, yes!” she said as she squirmed on the bed. “It feels so good, baby!”

“You want more?” he said teasing her. 

She gasped. “Please William! Please make me cum, baby!”

There was no way he was going to refuse such a request. He inserted a second finger alongside the first, fingerfucking her slower and more deliberately this time, letting her feel every nerve explode with pleasure. 

However, once she looked as though she was getting used to this rhythm, he curled his fingers and increased the speed of his pumping fingers considerably while he licked and kissed her folds and clit. 

She nearly flew off the bed, moaning intensely and reaching for him. William used his free hand to push her back down, his hand resting in the valley of her breasts. 

She groaned and lay back, clutching at the bedsheets. Her toes curled into the bed beside his shoulders and she tried desperately to keep her legs open for him. It was a pure, animal pleasure she was experiencing. 

William had one last trick he had saved for her. Just as she was getting close to what surely would be a tremendous orgasm, he suddenly sucked hard on her clit trapping it between his teeth as he flicked it with his tongue. 

She opened her mouth in surprise but nothing came out at first. Then she found her words;

“Fuck, William!” she screamed. “I’m going to cum! I’m going to CUUUMMM! OH, FUCK MEEE.”

William felt her body stiffen tighten. Her muscles gave way and she wrapped her thighs around his head. With a guttural groan, she came. 

William stopped to watch in wonder at the release she was experiencing. She clenched his fingers within her as she drenched both of them in her flood of fresh hot juices. 

This time William wasn’t going to give her the benefit of catching her breath. As soon as her orgasm subsided but before it completely went away, he moved up her panting heaving body. 

He instantly shoved his hard aching cock deep into her without warning. He sank full-length into her then as if bouncing off the bottom of her well, he immediately went to fucking her hard, fast and deep.

His hands were holding her hips as he pumped in and out of her like a deranged jackhammer. William looked down and watched as his cock began to sink into Ruth’s very hot and very willing pussy. 

Even though this was her occupation and she made her living doing this, her body tried to pull away from the hard cock invading her pussy. She had never been fucked so much and so thoroughly in one night as he had so far this one. 

But William held her in place forcing his cock head deeper into her wet quivering pussy, 

“Damn, you are one hot, sexy woman,” he said as he pressed more cock into her. 

Ruth moaned with both pleasure and appreciation as she felt her pussy forced open by this relentless, insatiable cock. 

William urged her onward, telling her to lay back and take it and the street whore slut in her began to comply. 

Ruth’s fingers gripped the sheets as his cock pressed still deeper into her ravaged body. Ruth couldn’t remember ever having any cock or thing pound this deep or this continuously. It was like he was a machine… he never seemed to tire or to finish! 

He withdrew a little and Ruth gulped a precious mouthful of air, still trying to handle all that was her body was being put through. 

But the respite was very short-lived as not more than a moment or two later, he began that wonderful fucking motion again. 

The muscles of her pussy had long since given up trying to resist him and now each stroke of his cock began to find her ever more willing pussy, as it accepted and welcomed this thick hard intruder, gripping it tightly as it slid in and out of her.

But William wasn’t a machine and the night had taken a toll on him. As Ruth lay there wondering how much longer this abuse could last the answer came in his announcement.

“I’m cumming honey! I’m going to cum!” he said as he thrust into her again.

“Oh god, William Yes! Oh please, please cum in my pussy! I need to feel you cum inside me!” she cried out.

He stopped for a moment looking down at her. “Are you sure sweetheart?” he asked. He was surprised–this was not how a girl of her occupation handled this sort of thing!

“Yes, baby. It’s okay, I’m on the pill and you said yourself you haven’t had much lately, so I figure you are pretty safe. Besides after everything you’ve done, I really want to feel you cum in me. Please?” she asked again.

William looked into the pleading soft brown eyes looking up at him. He kissed her lovingly and then resumed his fucking. Ruth lay back and got ready for it, her own orgasm rising quickly.

“Here I cum sweetheart! Get ready… here I CUM!” he growled. 

He slammed harder and deeper than ever into her holding himself in her as he shot a huge load of scalding hot sticky cum into her. 

The moment she felt him splashing her walls with his hot cum, she let go of herself and screamed out her own orgasm. 

As they clung desperately to each other their mutual fluids mixed inside her, the milky concoction seeping out from around his still pulsing cock to run down her legs to the crack of her ass.

Ruth clung to him holding him close as they went through their mutual orgasms and when they were finished she didn’t let go of him right away. 

He didn’t think much about it at the time but later that night when they went to dinner (to replenish their spent energy stores) she took his hand at the table.

“William baby, I just want to tell you that I have had the most amazing night with you. I have never–and I mean this–never had anyone who could make me do what I’ve done with you! You have made me cum so many times tonight, it’s a wonder I have the strength to eat!

“But aside from the sex, you seem to genuinely care that the girl you are with has a good time and you haven’t treated me like a piece of meat. 

“You have treated me very special tonight and never made me feel like a hooker… a whore. You made me feel like I am just a regular girl and that means a lot, believe me. I didn’t think I’d ever feel like that again. 

“Actually, you have treated me too well–I am going to hate going back to the streets again. Being just a cock sock to some joker with fifty bucks and a stiffy. 

“I’ve gotten a taste of the good life now and I like it. Thank you for showing me that life can be more than just a street corner.

“This job makes one very jaded and uncaring very quickly and I’ve been in this business for a long time. So to make me feel anything close to emotions is a tough thing to do,” she said. 

He listened carefully to her words and saw the solemn teary-eyed look in her face. He couldn’t resist her. He stood up and pulled her to him right there, wrapping her in a warm, loving embrace and kissing her like she was his girlfriend and not a rented sex toy.

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The pair spent the rest of the weekend together enjoying each other’s company and having wonderful times together. There was plenty of sex but interspersed with that, she showed him around Dallas and they enjoyed seeing the sights.

Far too soon for either of them, the weekend came to a close and it was time for them to go their separate ways. Ruth had to get back to work and William had a business to run.

“I want you to know darling, that I have had the best time with you–better than I think I’ve ever had with a man. 

“Thank you, William, thank you so much for a wonderful, amazing, beautiful weekend. I do hope you will come by and see me again. Please?” she said holding his face in her hand. 

She meant every word of it and he could it in her eyes.

“I will. And you promise you will be careful out here–I don’t want anything to happen to my girlfriend! And when I do come by, I have preferential treatment, right?” he said.

“Of course you do lover! And I think I like being your girlfriend!” she said. She kissed him once more but then she handed him something. He looked in his hand–it was the $500.00! 

“What’s this?” he asked.

“William darling, I know we agreed to 500 for the weekend, but that was when you were a customer. You never once treated me like this was a business deal. You treated me… well, I want you to keep your money, sweetheart. 

“Please keep it. For me. I wouldn’t feel right taking it from you now. Please, you haven’t treated me like a whore yet, please don’t start now,” she said and got out of the car. 

He drove away, looking back at her as she went back to her corner again.

As promised, he came by several times over the next couple of months, and they had wonderful times together. Then one day he came by her corner and saw her sitting there waiting for her next job.

“Hey there beautiful, you looking for a good time?” he said with a smile.

“Always! You looking for a playmate?” she said playing along.

“Sure, I could use a hot piece, hop in!” he said. As they drove off he turned and started heading a different direction.

“You get a new hotel room or something?” she asked curiously.

“No, the house I was having built finally got finished and I moved in last week. I wanted to show it to you,” he said.

They pulled up to his house and he took her inside. “Oh, it’s lovely! Oh, William, this house is a dream!” she said as she walked around. 

She touched everything and examined every detail telling him what she loved about the house in great detail. Then she went into the kitchen and pretended like she was the “little housewife” and he was coming home from work. 

“If I was your wife I would make sure your dinner was done, I would greet you at the door and take off your slippers and…”

“Why don’t you?” he asked suddenly.

She stopped suddenly. “What?” she asked, stunned.

“I said why don’t you? Why don’t you live here… with me?” he repeated.

“William, don’t poke fun!” she said, a little angry at his poor joke.

“I’m not poking fun. Why don’t you come and live here with me? You and I get along great and the sex is out of this world. 

“Ruth, darling, I just can’t live with the fact that you are out there on the streets doing what it is you do. It’s dangerous on so many levels and I don’t want anything to happen to you. 

“Don’t misunderstand me here. I’m not doing this out of pity for a poor girl on the skids or anything. I’m doing this because… well dammit, I really am fond of you and I want you to come live with me.

“I don’t know how you feel about me, but I know that we have wonderful times together and I just thought…” he said.

“OH WILLIAM, SWEETHEART, YES! Oh, Yes, I would LOVE to come live here with you! Oh baby!” she said before running off to the kitchen. 

William came in a minute or so later. “Ruth?” he said softly. She turned around and her face was wet with tears. “What’s wrong?” he asked.

“Nothing honey, nothing. I just never thought I’d… oh William!” she said, hugging him and kissing him over and over.

“Okay! Okay!” he said laughing. “Now we will have to go to your place and get your clothes and things–as hot as you look in that outfit, I don’t think you will want to wear it ALL the time! What say we save it for special occasions!”

“William, not to be a killjoy here, but if I am not working anymore, what do I do for money? I want to contribute if we are living together,” she said.

“Ruth, I am an old-school kinda guy. I believe that a woman’s place is in the home, taking care of the house, cooking and cleaning and that sort of thing. You know, like the typical ’50’s housewife. 

“If you can do that, I will take care of bringing in the income. Like I told you that first day, I make a very comfortable living–comfortable enough for two!” he said.

“Just call me June Cleaver then!” she said, kissing him again.
 

 

Published 5 years ago

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