This is the first of a 6 part story. The others are written so they will appear fairly soon. This is Shay Benson’s story. Escaping a difficult life, then meeting the young man who can change everything.
The car stopped outside the library, the one with the big lions outside. Shay Benson got out and tossed a thank you over her shoulder. The driver watched her tight young ass walk away and shouted,
“Thanks. That was fun last night.” Fun? To Shay it was just paying the price for a ride. She’d hitchhiked her way from the one stoplight town in North Carolina she’d called home to New York fuckin’ City itself. Sure she’d had to suck a few cocks along the way, like ol’ Pete back there, but when you’ve been sucking your Daddy’s cock since you were out of training bras, what was a couple more? It was when Daddy started taking more notice of her developing body and his caresses became more personal that Shay knew she needed to get out, see the world.
It’s not that she was afraid of the sex, her virginity had gone to Billy Mathews. The kid needed it and Shay wanted to be done with the whole messy thing, but Daddy? No, she was more aware of how things were supposed to work now. Mom was no help, cowed by Francis Benson and purposely oblivious to what went on. Shay had all the money she’d ever saved and the money Daddy had stashed out in the shed. She figured it was good back pay for cocks well sucked. And she’d need every bit of it in this city. She’d been amazed at the size as Pete drove them over the bridge. Now she was uncertain about her decision. Maybe a small town in the midwest would have been better. She wandered the streets for awhile dodging the onslaught of people, the maze of traffic, the peddlers and swindlers she was sure wanted to take her hard earned cash. Stopping for lunch, shocked at the prices, Shay realized she’d need work, soon. She had the name of a youth hostel, but even that wasn’t cheap. After lunch she followed the signs and worked her way downtown to find the hostel.
Her first night she slept fitfully. So much noise outside and much activity inside. She noted the young men looking her over. At 5-7 with long light brown hair, hazel eyes, B/C breasts and round ass she was sure to attract attention. Just out of high school she was still a teen who maybe knew too much about certain aspects of life. The next morning in the main room she took a look at her fellow boarders. Many were from other countries, visiting America, intending to see the world. Her eye was drawn to a table of youths speaking in some German or Scandinavian language, Shay didn’t know which. She’d apparently also drawn the attention of a tall flaxen haired boy sitting at that table. Shay liked blonde haired guys and this one with the pale blue eyes was just her type. When he smiled she was sure he could have his way with her. He made a gesture with his head asking Shay to join them. She walked with a tray of eggs and sausage to sit with the foreign guys.
“Hi. I’m Shay.” They all stopped chattering in their home language and welcomed the newcomer in perfect English, the tall blonde leading the way.
“Hello. I’m Sven. Please join us.”
“Thank you. I don’t know anyone here. I got here yesterday. Your English is so good, what other language were you speaking?” The guys were all smiling and talking. Sven answered directly,
“Swedish. We’re visiting from Sweden and spending a week in New York. They are all saying how they love your accent. You are not from New York?”
“No. I’m raised in North Carolina. Y’all have been in New York as much as I have.” When there was some more chatter in Swedish, Sven cut off his friends,
“No Swedish. This is perfect time to practice English. And no rude comments.” Then turning to Shay, “Apology for my friends. They didn’t realize American girls could be as pretty as Swedish girls.”
“Thanks. That’s sweet.”
“Would you like to join us today to visit Brooklyn Bridge and other places?”
“Well I do need to be looking for a job if I’m going to live here, but I think a day or two getting to know the city won’t hurt.”
“Very good. We’ll be happy to have you discover New York with us. Better for me than to just look at these guys all day.” They finished breakfast and started walking around Manhattan. It became obvious to Shay that Sven was the leader of the group and that he would be escorting Shay on their journey. When they stopped halfway across the bridge to look back at the skyline Sven’s arm was around Shay’s waist casually hanging on her hip. As she turned to walk he was there. He bent down from his 6-2 height and kissed her. After a moment’s hesitation Shay returned the kiss. His three friends walked on a little ways, leaving them to get to know each other a bit better. Now as they walked to catch up Shay was more pleased with this tall young man.
They had pizza and walked down along the seaport. The boys wouldn’t let Shay pay for anything. She accepted their good will as a way to save every dollar she had. As they walked north towards the hostel Sven, based on some of what Shay had told him during the day made an offer suggesting,
“We’ll be here a few more days. You can save some money and stay with us. It’s crowded, but we won’t mind.” Shay thought about it,
“Not much privacy.”
“We would not mind, if you don’t.” This could go so many ways. But a week free rent would help.
“OK, y’all just be nice.” When they got back Shay picked up her backpack and bag then moved down to the larger room the Swedes shared. There were 4 tiny beds. She looked around hands on hips. Sven smiled,
“You could share with me.” Shay sighed and moved her bags towards the bed he indicated. She looked at the other boys, fair haired Henrik, darker haired Erik, quiet Anders. They were each sitting on their own bed waiting. Shay laughed,
“You are all going to turn around while I change.” Disappointed they all turned from her. Shay quickly exchanged her shirt and jeans for a long t shirt and shorts. Now she sat on Sven’s bed and waited. “Should I turn around?” Sven answered.
“No, we’re not so shy at home. Nude saunas and hot tubs.” As he’d said the guys began cjannging,
unconcerned that Shay sat watching. She had to admit, they were a handsome group. When Sven, standing next to her, removed his pants she saw the clear outline of a nice sized cock. “Do you mind if I sleep in my underpants? I wasn’t planning on this arrangement you know.
“That’s ok.” Now the others were down to their shorts only. They waited, expectantly. Shay looked at them. Then a thought. Certainly they weren’t expecting. She looked at Sven.
“We’re all friends. The guys haven’t had anything since home.” There it was. “Men” she thought. At least these guys weren’t bad looking.
“I’m not fucking all four of you. But, get those cocks out and I’ll see what I can do.” In a flash, four sets of underpants hit the floor and Shay was surrounded by four hard cocks. One thing she noticed right away. Unlike most of the men she’d seen in America, these were all uncut. Henrik stepped forward and Shay took hold of his curved cock. She let her hand slide up and down, pulling his foreskin from the tip revealing a tender and waiting head. When she sucked him into her mouth he let out an audible groan. As she sucked him further into her, she felt hands on her tits and didn’t stop them as they lifted her shirt. Now her tits and nipples were being squeezed as she took Henrik deeper, much to his approval. It must have been awhile because he was soon pumping cum down her throat happy that she was sucking for each bit. Turning quickly she had Eric stop sucking on her tit to stand so that she could admire his thick cock. Not very long it was still more of a challenge than Henrik’s, causing her to keep her mouth wide open. When she felt a hand pushing into her shorts she slapped it away, then began working at Erik. She couldn’t get him as deep but used her tongue as she fondled his balls until he too offered up a healthy load. Now to Anders. He had nothing to be ashamed of, but after Erik he was a relief for Shay’s weary mouth. She was able to take him deep feeling his pubes tickling her nose. She rubbed his balls and coaxed him with her throat until he too spewed his cum deep into her mouth. Henrik, Erik and Anders backed up to their beds as Sven presented his longer, thicker cock.
“No, no blow job for you. I need that somewhere else.” Sven smiled and sat on the bed. Now giving up on privacy and modesty Shay removed the rest of her clothes and let the boys see her body. There were some comments in Swedish, but the nods indicated approval. Shay got in the small bed with Sven and forgot the audience as Sven began touching and caressing her. When he was ready he hovered over Shay as she lay back, bending her legs out of the way as his cock found the mark and split her wide as he entered. Shay moaned in approval then accepted Sven’s kisses as his cock went deep and wide. She’d avoided fucking anyone on her journey to New York so it was a pleasure to have a strong young man feeding a nice healthy cock into her. Sven had staying power and was able to bring Shay to the edge of orgasm a couple of times. Finally as he began thrusting hard, Shay let her hand find her clit and send her over the top. There were laughs of approval from the other side of the room at her gutteral sounds, followed by Sven’s grunts as he came, flooding Shay. As they came down, Sven sucked at her tits and caressed her sides until finally his wet cock fell from her. Satisfied, Shay snuggled up against Sven and fell asleep with his arms around her.
Shay had slept well. She woke confused for a moment, then felt the hand around her cupping her breast and a hard cock between her legs. She looked down at the hand, something was different. Shay leaned her head back. Dark hair? Erik! What the fuck. She started to turn, felt the thick cock rub between her legs, oh that was kind of nice. But what? She looked around the room. Anders was sleeping. Sven was standing, his cock dangling between his legs, holding his clothes.
“What the fuck Sven?” He shrugged.
“We’re all friends. We share. I got up in the night and Erik took my spot.” He shrugged again.
“So Erik has been behind me, holding my tits with his cock between my legs for how long?”
“I don’t know. It was dark, so I took his bed.” Now Erik propped his head on his hand. He moved his hips, letting his cock slide along her pussy.
“I ask before. May I?” Shay knew she should be mad, or cause a scene, but she remembered Erik’s thickness and he was oh so close and they were all so nice and damn, it was just sex. And sex was fun.
“Go ahead you Viking.” The words were barely out of her mouth when she felt herself being pried open by Erik’s invasion. “Oh fuck that’s good.” Encouraged, Erik began thrusting deeper. He couldn’t reach where Sven had but he was spreading her open at least as much. It felt wonderful. His free hand covered her tits, he had large hands, and he rolled her nipples between his fingers as he steadily pushed his cock deep then thrust. Moving on from her tits, Erik fucked her while rubbing her clit causing Shay to cum in a most satisfying way. As she stopped gasping, she opened her eyes to see Anders sitting, watching Erik’s cock disappear into her pussy, her dark hair now glistening from her moisture. Anders began pulling at his cock watching the show. Erik began to more frantically pump himself into Shay then let his cum shoot into her as his hand cupped her mound holding her in place. Feeling Erik’s cum inside and watching Anders stroking his cock, Shay called him over and as he kneeled by her bed she sucked a load from a happy Anders. Now as everyone lay about Shay considered her situation. If she stayed here, the boys being boys, she’d end up being their fuck toy the rest of the week. Was that fair trade for room and board? While sex was fun, she’d intended to find legitamate work in New York, not to prostitute herself out. She convinced herself that this was just young people having some sexy fun. But still.
“Guys, you’ve been lots of fun, but I think I need to be going.” They seemed disappointed. Their luck at finding a willing girl had run out. Henrik, now awake and not knowing what else he’d missed was sitting on his bed with morning wood. Anders said something to him in Swedish. He stood and walked towards Shay.
“Me too?” Shay thought, god dammit. Men, all alike. But this is what she’d known for some time now. Men have needs and somehow she was obligated to fulfill them. With a shrug she took hold of Henrik and soon had his cock in her throat and his cum in her stomach. Surely that was enough for all of them. She went and took a shower then packed up her things and said good-bye. Sven asked,
“Where will you go?”
“There are other hostels. And I need to find work.” Sven offered her money. “I ain’t a hooker.” But then thinking that times could get tough she gratefully accepted.
“Good luck Shay. I hope you find what you look for.”
What Shay was looking for was not easily found. Over the next few weeks she found waitressing jobs, but they usually involved handsy bosses and shift supervisors expecting the occasional blow job. Then one night she came back to where she was staying to find all her things had been stolen. The operators were no help. She was down to the clothes she wore, the money in her pocket and the prospect of having to fuck the restaurant owner for a raise. She was on a break reading through a local trash paper when she came upon a small add. Being New York you could find ads for all manner of escort services and barely concealed requests for sex. One caught her eye. ‘Young men looking for entertainer for high class party. Good pay. No whores.’ Rather specific.
Shay worked her next shift, endured the hands of the supervisor each time she walked by with her hands full and fended off his request for a little help in his office. She felt like she had a sign over her head. “Poor girl from the sticks, take advantage of me.” Surely with a different upbringing she would never put up with this, but it was now ingrained. Men were men and she did as requested. She thought of the ad. If she was going to take care of guys anyway, why not get paid? She called. After answering some questions she was given another number. A man answered. He couldn’t have been any older than Shay.
“Hi I’m calling about the ad. For the party?”
“OK, but you saw everything it said?”
“Yes.”
“So we want a nice girl.”
“I’m assuming I wouldn’t just be serving drinks, but you want a nice girl?”
“Yes. We can afford all the old hooker types we want, but we wanted something different.”
“We?”
“Yes, it’ll be a small party. A few friends. Send a photo.”
“I, um, don’t have a phone. I’m on a pay phone.”
“Interesting. Describe yourself.”
“I’m 18. 5 foot seven.”
“OK, but are you thin, fat, you know, breasts.”
“Yeah I got breasts.” He’d said ‘breasts’, hmm.
“Funny.”
“OK, I’m regular I guess. I ain’t flat, but they’re not huge. I ain’t fat at all.”
“Sounds good. You clean?” Shay thought about the Swedish boys.
“Yes.”
“OK. But I’m going to send you to an address for a test. We can’t be getting STDs.”
“OK.” He gave her the address for a clinic. This was getting more interesting.
“When you get a good result call here. Go soon, we want to set this up for the end of next week.”
“And, um, it said good pay?” He told her. She was shocked. Just who were these guys?
Shay went the next day to the clinic. Then followed up for the reults. She hadn’t gotten anything from anyone so that was a relief. When she called back she was given an address and a room number. When she looked up the address it was a very high class hotel in midtown. She was also told to go to a certain store and buy new clothes and charge it to the Frazier account. When she went to the store she realized the cost of her clothes would nearly match what they were going to pay her.
On the appointed day Shay arrived at the hotel and went to the room she was given. She was let in and told that this was her room for the night. A card on the table invited her to a party at a suite on an upper floor. Shay looked around her room, which was almost as big as her house in NC. The colors were muted and soft, the view was spectaular. She fell back on the bed and felt a level of luxury never experienced before.
Thoughts of maybe using her body to earn this kind of life crossed her mind. Shay changed into the specific outfit they had requested. Apparently they had some kind of a high school girl fetish. This would be easy enough to pull off. At 8:00 she followed the instructions up to the suite. When the door opened she was surprised to see what appeared to be five high school guys, food and buckets of champagne. And this suite was clearly larger than her childhood home. She was greeted by a teen who identified himself as Richard.
“Welcome. Everyone, Shay is here.” His voice was familiar. He must be the guy she’d been talking to. He introduced her around the room. Each guy well dressed, well groomed. Charles looked her over,
“Well done Richard. Wow.” Charles pulled her in for a kiss and a quick grope of her butt. “Nice.”
James was more polite, or not as forward, though Peter also allowed himself to sample the goods. That was four of them. Shay looked around the room and finally saw a blond haired boy, younger than her sitting in a chair, legs crossed observing.
“What’s his deal?” Richard answered,
“That’s Kent. He’s throwing this party for us. He paid for everything. He’s rich. Like really rich. His father is a lawyer for some of the most important people in the city. And hey, we’re all doing pretty well too. We all go to the same prep school. Shay looked over at Kent. He nodded to her. She felt she should say something.
“Thanks for the outfit and the room is amazing.” She got a smile in return. Richard explained.
“He’s a little quiet, but he’s no pushover.” They stood around sipping champagne and talking. Then at about 9, Charles took Shay by the hand and led her to the adjoining bedroom. It had all been so amazing she’d almost forgotten her role in this event.
“I’m going to take off your clothes Shay.”
“I guess you can do what you want.” At that Charles was all over her. Much less mature than Sven, he was all hands and lips, pulling at her school shirt and groping up under the skirt. “Hmm, slow down. Let me.” Shay more carefully removed her outer garments and let Charles see her in bra and panties.
“Oh my god.” Shay was realizing that while they may have money some of these guys were no more than high school kids. Shay moved to Charles and wrapped her arms behind his head. She kissed him lightly on the cheek.
“Are you ready for some fun?” She wasn’t sure if they’d ever hired high priced hookers like Richard indicated, because Charles here was ready to cum in his pants. Shay got down on one knee and undid his pants. He was pale and a little chubby, but smelled clean and fresh. When she pulled down his shorts a nice cock popped out at her. She smiled up at him and felt it and his balls. She stood, and told him, “Now you do me.” Charles hands were shaking as he fumbled with her bra, then down with her panties. He stared, and stared at her youthful breasts, her dark patch of hair, her long legs. She turned to let him see the curve of her butt then led him to the bed. “How do you want me?”
“Um, uh, however. It’s ok.” Now Shay was having fun with him. She got on her hands and knees, wiggled her ass, then rolled over and ran her hands over her mound, dipping a finger into her slit and bringing it up to her mouth. Charles couldn’t take any more and got right in between her legs. Shay offered enough moans and compliments as she could manage while Charles jammed his cock into her over and over. It didn’t take long until she felt him shudder and release his load. He sat back satisfied staring at her with wonder. He pulled on his pants while Shay used a tissue to clean herself. Then she followed him into the other room where time stopped as the other boys saw her, naked and ready. James was next and as before, he was polite and asked permission before touching her.
“James, I’m here for you. Have fun.” Shay was thankful that James was considerate and at least attempted to get her off too. She gave him that and rather enjoyed the way he pressed himself to her as he filled her pussy. She kissed him and thanked him for a good time, then went to the bathroom to clean up better. Five of them was going to be a bit much. She wasn’t sure if seconds were on the menu. When she came out of the bathroom Peter and Richard were waiting for her. She look at them confused. Richard explained,
“Peter and I do everything together.” Peter added,
“Everything.” So this would be different. Shay had never been with two men together and wans’t sure how exactly this was going to go. She started by sucking both cocks together. They seemed to have no problem with their cocks being held together as she licked and sucked at them. When she asked,
“Who’s first?” Richard said,
“Both.” Shay lay back and Richard got into position. He quickly buried his cock in Shay, then she was surprised to see Peter behind Richard. He had a tube with him and soon had Richard lubricated. Now as Richard pushed into Shay, Peter pushed into Richard. The pressure on her increased as the momentum from the two caused Richard to push hard and deep into Shay. She looked up to see Peter going fast and hard at Richard. The chain reaction of Peter filling Richard’s ass and Richard filling Shay’s pussy had them collapsing in a heap.
“Well I can tell y’all, I’ve never been in anything like that before.” She was watching as Peter sucked at Richard’s cock tasting Shay and Richard. Then when satisfied that Richard was ready Peter said,
“I’m going to wash up. Richard would like to fuck your ass.” Now Shay was taken aback. She’d never had one up her ass. But she hadn’t set any ground rules. Still….
“I don’t know. I never did that.” Peter whooped as he walked to the bathroom,
“Virgin ass. You lucky bastard Richard.” Richard was now caressing Shay’s body and especially her ass.
“You didn’t say there were rules against things.”
“I never thought.”
“That a bunch of guys wouldn’t want your ass?”
“Well no.”
“Don’t worry, I know how. Peter and I do it all the time.”
“So you’re…?”
“Gay? No. I just fucked your sweet pussy. Bisexual? Yes definitely. So much easier that way. Damn, I should have thought. If we’d brought another girl, would you have?”
“I never done that either.”
“How small was your town?”
“Small.”
“Well let me introduce you to the big city. On your knees.” Shay got on hands and knees, he butt in the air. As promised Richard took his time getting Shay ready. By the time he had a finger all the way in, Peter had returned and was sitting in front of Shay offering his cock to her. To take her mind off what was about to happen she began bobbing her head on Peter’s long slim cock. When Richard’s cock made it into her ass she was pushed forward and had Peter’s full length in her throat. Peter held her there, sighing with pleasure as Richard began going deeper. Shay was full now on both ends. Her asshole spread wide by Richard who was now slapping his body against her ass and Peter who was holding her head and fucking her mouth. Peter finished first cumming straight into Shay’s throat, then he got up alongside Richard and jammed a finger up his ass causing Richard to thrust all the way into Shay and fill her with cum. When they were done. She lay exhausted from the workout. She went in and washed up as best she could, cum leaking all over.
When she had everything under control she walked out again and looked at Kent. It seemed as though he hadn’t moved in the two hours Shay had been entertaining his friends.
“Are you ready Kent?” He looked at her. Not so much staring as appraising.
“Get dressed. Let’s take a walk.” Shay went back in and put herself together as much as possible. When she was ready Kent led her from the room. As they walked down the hall he asked,
“Did my friends treat you nice?”
“Yes. Sure. Where are we going?”
“We’re stopping at your room first. You can take a shower then put on your regular clothes.” Shay wondered if maybe Kent, though being a proper host and letting his friends go first, wanted her nice and fresh before he took his shot. Kent waited, sitting in a chair again as Shay took a long hot shower then put on the shirt and new jeans he’d paid for. The new sneakers too. She felt much more herself when she walked back out. Kent looked at her and smiled. He stood and took her hand. She followed him out of the room and up to the roof top restaurant. They were led immediately to a table. It was the kind of place without prices on the menu. As she pondered the menu he said,
“Get whatever you like. The lobster is excellent. We’ll have to drink iced tea though.” Lobster? Shay had never had lobster before, or a filet mignon. They ordered. Then as they waited she said.
“This is all so much. I feel so out of place.”
“You were out of place before. Tell me about yourself. Everything.” Shay thought. Why should she? She was hired company, but then the way Kent looked at her, so earnest, interested. She began. At the beginning. Living, not poor exactly, but with no luxuries. Then her father changing when she got to a certain age. What she did, had to do. And everything else right up through the hostel, her jobs until tonight. They were almost done with the main course when she finished. “Amazing. It explains a lot. I’ve had everything given to me. My father is so busy he gives me accounts with ridiculous money to spend to make up for his absence. Still, no one has ever abused me. It hurts to hear.”
“But you had no problem hiring me to have sex with your friends.”
“You’ve given me a new perspective.” Shay looked at him. She had high school but was an indifferent student. “A new way of seeing things.”
“Uh huh. You seem more mature than your friends.”
“It comes from my father. He expects me to follow in his footsteps.”
“Do you want to?”
“It wouldn’t be the worst life. First there will be an Ivy League school, then law school.”
“You must be smart.”
“In some ways. Book smart. But there are things I don’t know.” Shay picked at the last of her surf and turf. Kent looked at her admiringly. He had more to say,
“You don’t need to do that.”
“What?”
“Get paid. For sex.”
“Oh. Well it seems all I ever do is take care of guys’ needs to get anywhere.”
“You’re the most beautiful woman I’ve ever seen.”
“Oh stop. You don’t need to flatter me, you bought me lobster.”
“No. I’ve seen, seen mind you, many many women. Friends and famous associates of my father. I’d rather stare at you all night.”
“Just stare?”
“Perhaps more. At the appropriate time.”
“So you don’t want to? Are you, like with Richard …”
“And Peter? No, no that’s their thing. To each his own and all. No, I like women. I’ve been with some. Mainly because of who my father is. But you’re different.” He folded his hands under his chin and looked at Shay some more.
“I have to say it’s nice to have a guy looking at me and thinking I’m nice looking without also figuring out how to get his dick in my mouth.”
“You’re more than nice looking. Let’s go shopping tomorrow. I have accounts all over.” Shay laughed.
“That would be nice, but where would I even put everything. I told you my stuff was stolen at the hostel once already.”
“Ah, we have an extra apartment on the east side we don’t use. You can stay there.”
“What? How could I? What would your father say?”
“Nothing really. For one, he has places he’s forgotten about. Little places he used to take mistresses before Mother took her cut and left him. Now they’re empty. I may as well use them. And he won’t mind if I’m staying out of trouble, getting good grades and having fun. It assuages his conscience.”
“Assua–what? Sorry, no prep school.”
“He doesn’t feel so guilty.”
“So, what am I, your mistress?” Kent brightened.
“Why not? I’ve never had a mistress. I’ve hardly ever had a regular girlfriend. They all just want a piece of my money. You can be my mistress. I’ll lavish gifts on you and you can stay at the apartment until you figure out what you want to do.” Shay was shaking her head. This was all so much. A mistress to a teen barely an adult. But it sounded more comfortable than blowing a shift supervisor for a raise.
“I don’t know Kent. I might feel like..”
“Don’t say it. You’re not a prostitute or anything like that. You’re a person trying to overcome a difficult life. I’m offering a hand up.
“And what’s in it for you. Other than the sex.” He made a face.
“I’d be dishonest if I said I wasn’t sexually attracted to you. I told you, you’re beautiful. But you offer more. You know things I don’t. You have a different way of looking at things. And I’d want to take you to places I’ve seen but see them again with you. Museums and shows. I’ve been getting dragged to these by adults since I was little. It would be more fun with you.”
They’d finished dinner and were walking again. Shay had been thinking, now she commented,
“You make it sound so exciting. Can I ask you one thing?”
“Sure.”
“Why can’t I just be your girlfriend?” He shook his head.
“No. Not at first. My father wouldn’t approve. If you were my girlfriend then you would be expected at family events and he would not approve of me dating, no offense, someone of your status.”
“But a mistress is ok?” He looked at Shay with an embarrassed guilt.
“Yes. I was saying mistress in jest before, but in a way yes. He would not mind if I had a friend on the side to do whatever with as long as I didn’t get you pregnant and as long as you didn’t make demands. Anything else would be fine with him.”
“Such a different world.”
“So what do you think?”
“Let me see, I can either live in a dirty hostel giving blow jobs to get by or live in a nice apartment on a comfy bed and have fun with a nice guy who treats me like a princess.” He looked at her. “Yes, of course.” They continued walking, ending up back at the hotel. When they arrived at the door to Shay’s room she entered and turned waiting for Kent.
“Come in!”
“Thank you.”
“It’s your room.”
“No, it’s your room. Whatever you get is yours, nothing else implied. Whatever you give me is of your own free will. Agreed?”
“Well, yes. Sure. Would you like to stay?”
“I’d love to.” And now Kent smiled in a way he hadn’t all night. When Shay led him to bed he asked if he could just hold her and let her rest. She looked at him with his well groomed blond hair, slim build, kind eyes and let him take in her body. They lay together and spent the night kissing and caressing, then sleeping entwined together.
In the morning Shay woke lying on her side, the feeling of the soft sheets an extra pleasure on her bare skin. Beside her Kent lay on his back, the sheet barely covering him and a very promising tent in those sheets. Shay put her head on his shoulder and let her fingers trace lines on his bare chest, around his nipples then down to his stomach. She followed along the thin line of hair that diasappeared under the sheet. Kent woke to the light tickling and the pleasant sight of Shays bare breast against his arm. Seeing him awake Shay let her hand wander under the sheet until she encountered his hard cock.
“Mmm, is this for me?” Placing his hand on her breast a finger on the nipple he asked,
“Is this for me?”
“Uh huh, and I got another just like it if you want.”
“Ah, so nice to wake up and see you.”
“Will you make love to me?”
“I’m not really all that experienced. I was hoping that would be something you could teach me.”
“My pleasure, but for now, just let me feel this inside me.” Shay had wrapped her hand around Kent’s cock and squeezed it. He moaned and agreed. Kent was all smiles as he gazed down at Shay as his cock slid into her. For a short while neither worried about anything else and simply enjoyed the bare necessities. His cock, sliding in and out of her pussy. Both feeling pleasure they wanted to continue. Shay put her legs around Kent’s back and urged him deep, his cock a natural fit for her. When Kent let out a grunt and came Shay pulled him to her and held him tight as he throbbed in her. When he had moved back alongside he asked,
“Was that ok? Most girls fake things because of who I am.”
“It was real nice Kent. We can do other things and you can practice with me and it’ll all be wonderful.”
“You didn’t orgasm?” She didn’t want to hurt him, but he was used to people being phony wth him.
“Not this time. It doesn’t always happen.” He seemed dejected. “I’ll show you how. There’s nothing wrong with what you did, it felt great, but you can do other things and different things too. He was laying on his back staring at the ceiling. Shay straddled him and looked down into his gray eyes. “Hey, you want me to be real with you? No phony bullshit?” He nodded. She wondered if he was that used to not failing or not being told he failed. He nodded. “Well I’m a real person who will go on this adventure with you and you’ll do great just like you are at everything. I’ll be waking the neighbors before you know it, but I will not bullshit you.”
“You’re incredible.” She wondered if he meant her or her tits that were swinging above him.
“Thank you. I think you’re pretty great too.” Shay sat up and reached behind her finding his hanging ball sack. She held them in her hand rolling his balls. Getting the picture Kent reached up and began bouncing her tits, watching how they moved and swayed. Shay’s hand moved to Kent’s soft shaft finding that he was a bit of show-er. Her nails dragged along the underside of his cock as he pinched her nipples and rolled his thumbs over them. Shay shifted back and rubbed her slit the length of hes cock bringing new expressions of joy to Kent’s face. She had to remind herself that for all his money and worldly ways, he was a kid, certainly no older than herself. Shay used his cock for her pleasure making sure he rubbed along her and stimulated her. Kent was trying to hold on as Shay moved her hips back and forth using her own wetness to keep him slick as she glided along. Then leaning forward she pressed herself against him feeling it rising, spreading through her body, “mmm, uu-uhh-h, aiii, oh, ooh, mmm.” as she pressed one last time, hard, her body quivering, Kent came, spurting cum betweem them, coating her patch of hair, up to his stomach.
“Oh shit sorry.”
“Noooo, no not at all. That was a real orgasm. I felt wonderful.”
“But I..”
“Came on me? That’s ok. You can do that anytime you want.” She lay on Kent, not worrying about the cum sticking between them, kissing him in thanks for sharing the moment. “When I invite you to my bed we can try anything you want. Well, within reason. I even let Richard fuck my ass the last night. Now that was different.”
“He what?”
“Yeah, right after Peter fucked him in the ass.”
“Those two are crazy.”
“All in the past now, right?”
“Right, you don’t have to do anything you don’t want to do.” Shay smiled at Kent. Then put her head down on him to be sure she didn’t cry.
“Thanks.”
They showered and dressed, then went out shopping. Shay tried to explain that she just needed plain clothes, shirts and jeans and such.
“But what if I want to take you someplace special. You’ll need dresses and shoes and whatever ever else women wear.” Shay had never had fancy dresses or a need for them. “Let me make a call. One of my father’s assistants, she’ll know where to go.” He put a finger up,
“Monica? It’s Kent. I need some advice. I’m with someone and I’d like to get her something nice for evening wear. Uh huh. She’s 18 or 19? Tall. Yes. OK, thanks. Ask for Charice? Thanks a million. No, Dad doesn’t know. OK, sure.” Kent took Shay by the hand, marching up and down streets and avenues until they came to a boutique that didn’t need to have it’s name on the window. “Monica says we ask for Charice and tell her you need something formal and something for a party. Then she’ll take care of you.”
Once inside and with a plan Kent became his confident self. He told Charice that he and Shay would be attending a theater opening one night and then a party at a private club another. Charice took over from there measuring Shay and showing her different styles. The longer more formal dresses were fine with her but when Charice brought out the slinky dark party dress Shay about died,
“Oh my god, I can’t imagine myself in this.” Charice looked at her,
“Honey, with those legs and your bosom, Kent over there will be fighting them off. But you’re going to need the right undergarments for the full effect. Shay had never worn a thong or a strapless bra. They weren’t needed under a t shirt and jeans. Once Charice got her comfortable and slipped the dress over her, Shay turned to look in the mirror. The effect made her blush. The dress was short and form fitting and just perfect. Slipping on heels Shay stepped out to show Kent.
“Oh wow, the most beautiful woman I’ve seen.” Charice smiled at him,
“I’m not going to argue with you on that. She’s a sexy one.” Everything went on the Frazier tab. Shay didn’t know just how much, there were no labels on the clothes. They moved on to other shops for designer jeans that hugged her butt perfectly and more shirts and undergarments. When they stopped for lunch it took both of them to carry it all. When they finally turned up a street and stopped before an apartment building Shay asked,
“Where are we?”
“Your new home.” Looking up and down the street at the wealthy looking neighbors Shay shook her head.
“You can’t be serious.”
“Sure, let’s go upstairs.” Kent produced a key. They took a small elevator up to the top 4th floor. It opened onto the foyer of a large apartment. They dropped the bags on the floor and took a quick look around. “The view isn’t great, but the neighborhood is safe.”
Shay spun around in the middle of the living room. Then ran to Kent taking him in her arms, kissing him and thanking him. She had his belt open and his pants down as she sank to her knees. Kent stopped her,
“No. That won’t do. You don’t have to do that just because a guy does you a favor.”
“A favor? This is life changing. I was blowing my Dad for a few dollars allowance and sucking guys for a ride. This is amazing.”
“So. I did it because I wanted to, not because I wanted something. It’s different. I don’t want to feel like I’m buying favors.”
“Can I fuck you because you’re a great guy and kinda nice looking too?”
“If I can fuck you because you’re funny and pretty and sexy as hell.”
“Can I give you a blow job for the hell of it?”
“Not until you teach me how to get you off eating pussy.” Shay grabbed his hand,
“Then let’s go, there must be a bed hidden somewhere around here.” They were naked and spread out on a large bed. Kent was eagerly licking at Shay’s pussy, kissing anything he could find. She let him have his fun, then told him where to concentrate. A smart kid, he learned fast and after a bit of effort was rewarded with Shay holding his head with her legs and drenching his face as she screamed with pleasure.
“Oh fuck, Kent. that can’t be faked.”
“I’ll do it again, you’re so tasty.”
“Thanks, but I really want to reward you for a job well done.” Shay brought him up to her, kissing him and tasting herself. Then working her way down his body, kissing and licking and biting down and down until she reached his hard cock. Licking up one side then down the other, taking one ball then the other into her mouth, kissing his shaft to the top and teasing his opening with the tip of her tongue, wrapping it around his head then sucking it into her mouth. She looked up at him with her hazel eyes, never losing him as she lowered herself down, concentrating to get every inch, feeling his head just past where she might gag, pressing he nose against his hair, using the muscles in her throat to hold him, then slowly letting him feel his cock slide out along her tongue. When she at last popped his head out from between her lips she smiled at Kent then began bobbing on him, fondling his balls, letting her fingers, press and prod underneath him, causing him to moan and clench and tense, then his balls drawing up, the cock in her mouth throbbing, Shay taking him deep again, coaxing him, willing him to reward her efforts. With a sign and a push of his hips Kent was in her throat and pumping cum in spurts. Shay swallowed and swallowed savoring every drop, milking him, sucking all the way up. “How was that?”
“Oh my god, damn wow.”
“I guess I passed?” Now they wrestled and played like two naked teens would, with much fondling and touching of firm young bodies. When they rested, a bit disheveled from their play, laying alongside each other catching their breath, Kent propped himself on a elbow.
“What?”
“I need to keep looking at you, to be sure it’s all real.”
“Oh stop. OK, in my vain moments I look in a mirror and think I look pretty good, but you go overboard.”
“Nope. We did the sex thing and it’s not wearing off. Still beautiful.”
“Oh shit, you’re so funny. But when you can get that thing hard again we can do the sex thing again.”
“I can hardly wait.” They did the sex thing again. Then they walked around the apartment naked so Shay could figure out where everything was. To say it was a four room apartment wasn’t fair. It was a huge four room apartment. It took up the whole floor with modern furniture and appliances.
“And I can just live here and no one will care?”
“Yep, no big deal. Better than it being empty. The cleaning woman comes Tuesdays. I gave Monica your name so there won’t be a problem with security.”
“This is just…just ridiculous. Talk about going from the basement to the penthouse.” Kent shrugged. It would take some getting used to how casual he was about large sums of money. They dug through the bags, Kent finding the box with the phone.
“Let’s get this setup. There’s wifi here and then I’ll be able to call you.” Shay sat in silence. “What’s the matter?” Shay almost smiled as she looked over to see a naked Kent, his well used cock hanging limp while he worked on opening the box.
“I ain’t really ever used the internet. I’ve seen it on other people’s but we didn’t have a computer and our school was just getting them from some government program when I left.”
“No problem, I’ll show you. We’ll get you a laptop. I use mine all the time, but I won’t need it for porn anymore because you’re way better than porn.”
“Oh shit Kent you’re making me laugh.” Which was fine with Kent because he liked the way her tits jiggled when she laughed. Finally getting the box open he sat next to her on the sofa and set up her first cell phone. First he showed Shay the basics. Then they took a bunch of pictures of themselves naked, then they laughed at all the naked photos. “Can those be deleted now?”
“Oh no, their all over the internet. Some kid in Japan in wacking off to you right now.” Shay gave him a look of some concern. “Nah I’m kidding. Here, this is how you delete them. Now if you SEND them to someone, other than me, they may end up everywhere.”
“I can send naked pictures to you?”
“Oh shit, not too many or I’ll flunk out of school.”
“Hmm.”
“But I’d rather see you naked in person anyway.” This led to much tickling on the sofa, then on the floor, then some serious kissing on the thick rug. They finally got around to putting away Shay’s new clothes. Found that there was some fresh food in the fridge and pantry and set about putting together some dinner. Shay put on the apron,
“Burning your tits off is not recommended”, and twirled around the kitchen giving Kent peeks at her bare bottom. They ate, then watched the large flat screen TV, then at about 10, Kent made the sad announcement.
“I need to get home. School in the morning. You can come and go of course. Wednesday Charice will have your evening wear ready. Friday is the opening of a new Broadway show. I have tickets. You’ll make your grand appearance.”
“Grand appearance?”
“We’ll go in before the stars and all but still, it’s a scene.”
“I better practice walking in those heels.”
“Or you’ll really make the news.”
“I wish you didn’t have to leave.” His shoulders slumped.
“Don’t be sad. I’ll see you soon.” Kent was dressed now. Shay wore a long t shirt. He kissed her good night and was gone through the elevator. Shay looked around. A bit of a step up from a youth hostel. She watched a bit more TV then was off to bed.
Monday Shay walked the neighborhood. Sooner or later she’d need to find a job, to have something to do other than sit around in luxury waiting for Kent to show up. Not that she would mind having Kent show up. After a lifetime, or as much as an 18 year old can have, of sex for physical need or to pay back some needy guy, Shay was having sex for fun, for pleasure, because she wanted to. She appreciated all Kent had done for her, from the moment he’d said, “You don’t need to do that anymore”. Still it seemed odd. He WAS giving her food and clothes and a beautiful place to live. She didn’t feel taken advantage of, but then he was younger. Was she taking advantage of Kent who though he was rich and somewhat wordly was also a naive kid. I was all so confusing.
Kent called in the late afternoon. He had too much schoolwork and wouldn’t be over. He asked if she needed anything. He said he missed her. Shay hoped he missed her. All of her. She was missing him. With his jokes and his inability to recognize just what he had. By Tuesday afternoon Shay had had enough TV, enough of the phone that already felt like an extension of her hand. Not that she had anyone to call or text, but the internet was habit forming. But right about 3 pm she was needing companionship. When the elevator started up she decided to show Kent just how much she needed him. She stripped down and as the door from the foyer opened she ran to greet him. Except that him was a middle aged man with a briefcase. Shay stood naked with hands on hips,
“Who are you?”
“I could ask the same, but I already know. You must be Shay.”
“I am.”
“And I am the owner of this apartment, William Frazier.”
“Oh shit, I’m sorry.” Now Shay was trying to cover herself and running to find a shirt.”
“Nevermind young lady. I may as well see what all the fuss is about.” William put his briefcase on the hall table and followed Shay into the living room. She had her shirt in hand.
“Really?”
“You didn’t seem fussed about it before you knew who I was.”
“I didn’t expect. I thought you were…”
“Yes, Kent. My son who hands out my properties like candies and spends my money like I have an endless supply. Fortunately I do. Now let me get a look at you.”
“Please may I dress?”
“Yes go ahead. I can see why my son is enamored with you. Of course Monica told me what was going on. Sit. Sit.” William took a chair and watched as Shay curled up on the sofa. “He does have good taste. Now let’s see if he has any sense.”
“What do you mean?”
“I have only a few rules for him. One is don’t get anyone pregnant and another is don’t make us a laughing stock. Now are you on some kind of protection?”
“Yes.”
“Good. I’ll give you a card to see a physician. I want to be sure everything is in order.”
“I recently went.”
“Yes. Dr. Evans. He’s ok, but I want a full exam not a quick blood test and I want to be sure you won’t be hitting Kent with a paternity suit.”
“Really now.”
“I don’t know you from Eve and the first time I met you you weren’t even wearing a fig leaf.” Shay stared at him. She got the reference. If there was one thing you got in rural NC it was some church learning as a child. “I’ll talk to Kent some more to get a better judgment on his intentions. I’m perfectly fine with him having someone for fun, lord knows I’ve had enough of my own in places like this. But I hear he’s buying you gowns? Does he plan to take you to public events?”
“I, yes, he did say something about the theater and a party.”
“Hmm. You don’t have any record. And I don’t think you’ve been married. No kids?”
“Mr. Frazier, I’m 18 and just left home.”
“And you show up in New York and latch right on to Kent Frazier. Convenient. Some might use other words.”
“I’ve had a rough upbringing. That I’ll admit. Abuse at home, from my father. That’s why I left, before it went further.”
“Hold out your arms.” Shay did while asking why. William took her wrists and turned her arms back and forth. It hit Shay what he was looking for,
“I’ve never done drugs.”
“My doctor will know if there’s anything in your system. You drink?”
“Only what your son and his friends gave me recently.”
“Hmm, don’t be smart with me.”
“I’m sorry, no not much. Wine, beer now and then.”
“Do you have the dress for the theater?”
“No, I pick them up tomorrow.”
“Go inside, fix yourself up and put on some nice clothes. I’ve seen your birthday suit. I’ll wait.” Shay wondered if she detected a bit of Kent’s sense of humor. She did as asked and came out a bit later in stylish jeans and nice blouse, pumps and her hair and makeup in place.
“OK?”
“You’re obviously from a different social class, but you are attractive and will not make Kent look bad. OK, get the dresses and you may attend the show with him.”
“Thank you.” William looked around the living room.
“Ah, if these walls could talk. Then again you might run right out. You can stay here. Just don’t toy with my son and don’t take advantage of him. There’s no need to, he’ll take care of all of your needs if he’s as smitten as he seems.”
“He’s a great guy. Kind, generous.”
“And in less than a year he’s going to college and starting on a career. What are you doing?”
“I’m planning to find a job. I find sitting here all day a bit of a chore.”
“I might be able to help. What are your work experiences?”
“Waitressing mostly.”
“Hmm, so call girl was a one time thing?” Shay turned a deep red. Then she started to cry. He hard exterior cracking.
“Please, I was desperate. My things were stolen, my supervisor at the restaurant was pressuring me for sex and I’d be sorry if it wasn’t what led me to Kent.” He handed her a tissue.
“See the doctor. I might know someone who could use an attractive hostess for his restaurant.”
“Thank you.” They heard the door open. Kent entered the living room carrying a box containing a laptop.
“Shay! I got you….Dad? What are you doing here?” Now concern registered on Kent’s face. As much as he had his freedom, his father’s word was final in all matters once he got involved.
“I was catching up with your lady friend. I need to know who’s going to be living in one of my apartments.” Kent visibly relaxed. He put down the box and went to stand with Shay. When she put her arm around his waist, William looked at his son and the pretty girl and nodded.
“I’ll let myself out. Oh and one more thing. Call to have someone put a lock on the foyer door so someone can’t come right in from the elevator. You don’t need any surprises.” Then with a grin he was gone.
“What was that all about?”
“Um, I thought it was you earlier. Your father may have gotten a good look at me.”
“He what?”
“Ye-ah, everything.”
“Was he impressed?” Shay slapped his arm.
“The only important thing is, are you impressed?”
“Why did you get dressed up?”
“He wanted to decide if I was ok to go out in public with you.”
“And?”
“I didn’t spit on the floor or scratch my crotch so I think we’re ok.”
“We should have dinner. There’s an Italian place around the block down in a basement.”
“MMM, sounds good. Should we fuck then have dinner or have dinner, then fuck, because I sure am getting laid tonight.” They came togther in a whirl of discarded clothes. Dinner would wait. When Shay was naked she leaned over the end of the sofa and begged Kent to take her right there. Standing behind her he caressed her butt then aimed his cock and took her deep and fast. He was able to give Shay long strokes straight in holding one hand on her ass and one on her hip. As he slammed forward he looked to the side to watch her tits swing forward and back, until Shay rested her head on her arms and let Kent drive into her. When he began short fast thrusts she waited, then he held her hips tight and fucked her hard as he came. “Uh damn I needed that.”
“Me too. I couldn’t concentrate today thinking about you.” Dinner was followed by more frolicking in bed. It got late quickly. Kent had to go but promised to come over the next night to setup the laptop. He almost didn’t make it out the door finding it hard to walk away from Shay.
But there were rules he couldn’t break if he wanted to continue having fun. Finishing at the top of his class was one of them.