Shelby gets an offer she can't refuse, starting her down the path of sexual adventure
I've edited and updated this first chapter - posted on 23 May 14. It has new material and has been reworked a little so I can continue the series per request of many readers. I will be updating a chapter ever couple of days until I have chapter 7 updated. Then I will be adding new chapters for those who like the series.
Sixteen year old Shelby was sitting home alone watching a show on HBO. Her dad was working his series of shifts in Houston. He wouldn’t be home until Monday. Shelby had another two hours before her shift at work. It had been a short day at school so she was enjoying a leisurely afternoon.
The blond haired girl was sitting in her father’s easy chair with her small calico cat Squeaky sitting in her lap. The small female cat was purring away as Shelby absently stroked her fur.
Shelby was watching an episode of ‘Game of Thrones’ which was actually recorded on the DVR the night before. She really liked the series; Shelby was a stalwart science fiction fantasy fan when it came to her casual reading and George R. R. Martin was one of her favorite authors.
Shelby had been feeling horny all morning—she woke up horny. She chocked it off to having a sexy dream before waking. She didn’t remember the details of her dream, but she was still affected by its flavor.
Having been finished with her chores around the house, she took a shower and dressed in her waitress uniform in preparation for work. The garb was a nondescript classical waitress style dress that did nothing to show off her lithe, athletic body.
Being alone, Shelby’s hand kept finding its way between her legs, gathering up the skirt of her dress giving her fingers access to her undergarment beneath. She would subconsciously tease herself through the panel of her panties until it occurred to her what she was doing; then she would withdraw her hand.
It wasn’t until the show she was watching showed a really steamy sex scene that her fingers went from autopilot to active flight controls. Shelby pulled her dress up again and started to rub over her cloth covered clit in earnest.
Not getting the result she wanted, she pulled her panties to the side, and after wetting her fingers down inside her vaginal opening she began some serious masturbation. The sex scene was turning out to be protracted, which only added to Shelby’s growing passion.
Even as the show moved on, Shelby’s fingers did not. She closed her eyes, replaying the love making scene she just viewed inside her head. She began to rub her breasts through the cloth of her dress as she continued to dig at her pussy.
Shelby felt herself become delightfully wet as she felt the familiar pressure build up inside her vagina. As she continued towards her goal of an orgasm, she gave herself a mental task to change her panties before heading for work. It wouldn’t do to walk around the restaurant smelling like her musk during her shift at work.
The closer Shelby came to cumming, the more aggressive she became with her fingers. Squeaky, annoyed by the motion in her resting spot had moved to higher ground--the back of Shelby’s chair. The small calico, in her new location, twitched her tail in irritation.
Shelby feeling the pressure inside her tummy reaching a nearly unbearable level started to writhe; she knew she was seconds from relief. Then it happened, the pressure inside her vagina abruptly released. Shelby gasped as she felt the entire length of her inner canal begin to spasm and ripple. Waves of pleasure poured out throughout her body. Her thighs wrapped tightly around her hand, which was still embedded in her pussy lips.
The teenage girl moaned and whimpered as she quaked in her daddy’s easy chair. Shelby found relief to her horniness; orgasms always amazed her ever since she discovered them after turning thirteen years old. After ten plus seconds, her gratifying climax began to ebb, leaving the girl to melt back into the chair to enjoy the afterglow.
Pulling her fingers out from underneath her dress, she noticed how soaked her digits were from the prodigious moisture her vagina produced as she came.
Bringing her fingers to her nose she sniffed. She giggled; changing her panties was definitely in order.
Shelby lived with her father, Eric Krueger her father in Conroe, Texas, a bedroom community north of Houston. Shelby’s mother died when she was ten, leaving her to live alone with her dad who did everything in his ability to provide for Shelby, his only daughter.
When Shelby’s mother died in a tragic car accident, there was a large life insurance settlement. The $650,000 Shelby’s dad received was mostly from a $500,000 accidental death policy, with the remainder coming from $150,000 term life policy that was part of his wife’s benefit package provided at her employment. In addition, Shelby’s mother had a large 401k that her dad inherited, containing nearly $280,000.
Eric invested the insurance money to provide income. With what was left of the 401k money after the IRS took their cut, Shelby’s dad bought a nice house in the moderate sized city outside of Houston. He wanted Shelby to grow up somewhere fairly free of the crime and corruption that one could find in the larger metropolis.
Shelby locked up that house as she exited through the door wearing a fresh pair of panties under her waitress dress. She climbed on her bicycle and rode to the corner and stood in front of the Churches Chicken and turned north as she continued her bike ride to work.
On the bicycle ride she was thinking about the new school year that had just begun. She was starting her junior year. Shelby was a brainy girl, She was proud of her 4.0 grade point average she maintained her freshman and sophomore years. She was hoping she would continue the same success as she took a large number of advanced placement classes during the current year.
With an August 21st birthday, Shelby was one of the youngest students in her class; she had just barely turned sixteen when the school year started.
Shelby went to school at Conroe High School, which was a large 5A school. Her class had over 1000 students, and with other class year of equal size, getting to know all everyone in her school, let alone her class, would have been impossible.
The blond haired, blue eyed Shelby was outgoing, so she had a large subset of kids as her friends and or acquaintances. She really had no one she would consider an enemy, although there were kids she didn’t like.
As Shelby continued to ride on, her mind turned to getting a driver’s license. She was enrolled in driver’s education at school. That would put her one step closer to her goal.
The main reason to get her license was so it would be easier for her to get to work. The McIntyre truck stop was just off of I-45. I-45 was a busy corridor that ran through the west side of Conroe winding its way down from Dallas heading to Houston. Shelby worked in the truck stop’s large sit down restaurant, which was frequented by thousands of travelers a month, as well as a good number of locals.
She had already been out on the road twice with her instructor, and she thought driving was one of the most exciting things she had ever done. Her dad said that once she had her license, he would help her find her an older model car that was in decent shape.
Shelby rolled up to the truck stop and locked her bike to the light pole outside the entrance to the office where she would clock in. Shelby began her short walk to the restaurant. She always looked forward to doing her shift.
Shelby had been working at the restaurant since she was fifteen; she was originally was hired as a bus girl. Because of a fluke, she ended up taking a shift as a much needed waitress.
The standard waitress fail to show for work one evening, and the manager had no choice but to try Shelby out in the position. Shelby had been working at the busy restaurant for only six months.
The manager discovered that the pretty, outgoing girl was a natural. She could keep track of orders and never failed to arrive at the right time for refills or when there were other needs at her assigned tables.
The girl was offered the waitress position permanently the second time the same waitress failed to show for her shift again and was fired. This was all before Shelby turned sixteen.
Shelby quickly got to know all the staff to the truck stop and really enjoyed working there. She enjoyed meeting all sorts of people, and she befriended almost all her coworkers.
With that said, the person who intrigued Shelby the most was Liza Stone, a fellow waitress in her early to mid-thirties who had been working in the restaurant for a little over a year.
It was rumored that Liza turned tricks with various regular customers. What fascinated Shelby was that someone would do THAT for money.
In Shelby’s opinion, Liza was a good looking woman who was well built. Although Liza wasn’t a beauty by any means, she wasn’t a bad looking ‘lady’ either. She was more than good looking enough for the middle aged gentlemen she allegedly did business with.
Once clocked in. Shelby walked through the convenience store on her way to the restaurant. She had five minutes before her shift started. Her mind still on her coworker as her body did its required tasks, totally on autopilot.
Shelby had several discussions with Liza over the prior year, usually during the quiet times during the late evenings. The two would talk when the crowd dwindled down to just a few customers.
Liza didn’t hide the fact that she went to bed with guys for money. She considered herself and independent business woman who dealt with a stable client base. Once she had built up her group of regular customers, she rarely took on a new client.
Lisa disclosed to Shelby that she made as much doing business on the side as she did from working as a waitress.
Shelby asked her why she did it and was astonished with Liza’s answer, “It’s because I love sex. I could fuck two or three times a day; I could still come back for more. I just figured what the hell, I might as well get paid for what I enjoy doing.”
This got Shelby wondering if she could ever do THAT, drop her panties for a complete stranger for money. Little did she know that she would be put to the test that very evening. She would be put in a position where that exact question would be postulated.
It was a Friday evening, Shelby was scheduled to work until 9:00pm. Then she would head home and start her weekend. She spent five minutes with the waitress she was taking over for, getting an accounting of all her tables. With the tables turned over to Shelby, the girl got to work.
As the evening progressed, it looked like a good shift for Shelby; she had a lot of customers with steady tips flowing in. It looked like she was going to accumulate a nice haul for the evening.
Because of School, Shelby couldn’t work a lot of hours, mostly just evenings during the dinner rush and weekends. So getting a good night of tips was always welcome.
Around 7:00pm, Shelby approached the hot food rack to pick up her order for table 36. Liza who was standing there whispered to her, “Hey, the guy at table 28 is Sandy Jordan; he’s a regular and has been asking about you. You might want to drop by his table when you head for your break, you know, just to hear what he has to say.” Then she paused and then said, “I think you might find it worth your while.”
Shelby responded, “Um, okay, um, thanks Liza.”
Shelby pretty much knew what Liza considered ‘worth your while’ to mean. Was Liza throwing her what the woman considered was a bone? What Shelby pondered was whether or not she would pick it up and chew on it?
Surprising herself, Shelby decided to hear the man out. Ten minutes later, the manager told the girl to take her break. So, with huge butterflies in her tummy, Shelby approached the man at station 28.
She smiled nervously at the man; he was a pleasant looking fellow that she guessed was in his mid-forties. He looked much better dressed than the average trucker or tourist type they got through the restaurant all the time; he looked like a successful businessman. She asked, “Hi, are you Mr. Jordan?” He smiled and nodded yes. Shelby anxiously continued, “Liza said you wanted to talk to me?”
Sandy smiled and said, “You, my girl, are an absolutely gorgeous young woman. You’re so tall, and, um, so blond.”
Shelby blushed and said, “Um, thanks. I think.”
The man said, “Well Shelby, it is Shelby isn’t it?” Shelby nodded yes. Sandy continued, “Well, I’ve been traveling through here every week for the last six or seven months. I have a sales route between Dallas, San Antonio, and Houston. So I am traveling to Houston fairly often.”
Then he hesitated, “What I’m doing such a poor job of getting at is that I tend to get lonely on the road. Do you understand what I’m saying?” Shelby gulped and nodded her head yes.
He continued, “Well, Shelby, I’m hoping you might help relieve me of some of that loneliness. Do you think you could do that?”
Shelby was feeling a bit cornered, but she also was more than a little intrigued. The purpose of the conversation, as Shelby suspected, was out on the table; the girl was sure the man was propositioning her.
The man seemed to get right to the point. Shelby decided he was pretty confident of himself, so she wanted to hear the pitch, “Okay, so what do you have in mind? How do you think I could help you with your, um, loneliness?”
“Well, I was thinking.” the man said, “While I’m in Houston, we could meet up on a regular basis.” Sandy continued, “You could dress up nicely and we could have an enjoyable evening on the town.
“If the mood is right, afterwards, we could go to my hotel room and have a pleasurable evening.” Then he thought about how he could say it delicately, this was where he either hooked the girl, or sent her running in fright. He added, “In return, you would be well compensated.”
Shelby was fascinated, “What are we talking about when you say that I would be well compensated?”
Sandy laid out the terms, “Okay, here it is. I will give you $250 a visit whether we visit my room or not. I’m not always looking to assuage my loneliness in an intimate manner; sometimes I just want to have someone to spend time with. If we do end going to my room for anything more than conversation, then you will get an additional $250.
“I usually get into Houston about 5:00pm, so we would normally meet up around 7:00pm. Then we could go out and have a nice dinner, maybe catch a movie, the theater, or maybe an occasional concert; then see what develops after that.”
Sandy added, “What I’m looking for is a steady date, Shelby; someone I can see regularly when I’m down this way. That way I know what I’m getting—I like tall girls like you. By us setting up a steady arrangement, I don’t have to hunt down someone new every time.”
She blushed, “Um, you do realized: A, I’m still in high school—I’m only sixteen, and B, I’ve never spent an evening with a, um, gentleman, or with a boy for that matter.”
Sandy smiled, “Well, I can see where those could be problems, but I don’t think they’re insurmountable. As for the first one, if you don’t tell anyone your age, I won’t. Because you are a bit young, I’ll even add another $100 for regular visits with you if we hang around my Hotel room for more than a chat.”
Then the man got a serious, yet a kindly look on his face, “As far as it being your first time, well it would be a real honor for me, Shelby, a real honor indeed. You come spend the night with me, and I’ll make it worth your while, I’ll give you a $1000.”
Shelby figured she would have the whole idea nipped in the bud. Planning on chasing the man away with an unreasonable counter offer, the girl grinned and said, “Not a penny less than $2500 and that’s only if we include all the entertainment—a dinner and a movie. For that amount, we only spend two additional hours together, and then I come home.”
In direct opposition to the idea that she was trying to squelch the whole idea, she added “It isn’t every day you can take a girl’s virginity.”
Sandy smiled, “Well, now we’re negotiating, I like that.” The man thought it over for a minute; he really wanted the girl’s flower.
He decided to sweeten the pot so he could get what he wanted, he laid out the deal, “Getting to take a girl for the first time is a unique–that’s valuable all by itself; I’ll give you that. How about I agree to your $2500, but then I throw in another $500 so we can spend the entire night together. For $3000, I get your cherry, and we relieve my loneliness until I’m totally gratified.”
Shelby was astounded that her offer had been accepted; she was blown away that someone would pay her so much money to take her virginity. The offer was surreal—she wanted the money. Even so, Shelby was still a bit hesitant. As avaricious as she was, she didn’t know the man from Adam. In addition, she was conflicted, she still didn’t know if she wanted to copulate for money.
Making up her mind, Shelby decided that if Liza knew him she figured she would be relatively safe. She made one last demand; if met, she would go with the stranger.
She laid out her final condition, “I will only agree to those terms if I can get a copy of your driver’s license and vehicle registration; we leave it here with Liza, the waitress who arranged this discussion. That way if I end up missing, I can have someone send out the posse and they will know exactly who to hunt for.”
Sandy smiled, “You’re an intelligent girl! You don’t know me whatsoever, so protecting yourself is smart, very smart.” He hesitated a second and then grinned, “Deal!” He stuck out his hand for Shelby to shake.
The girl hesitantly reached out her hand and shook it. The deal was struck; Shelby was going to lose her virginity.
Shelby informed Sandy that she didn’t get off until 9:00pm. He smiled and said, “Okay, I’ll wait.” Then he asked, “What size dress do you wear?”
Shelby, being a tall girl at just a quarter inch under 5’-10”, said, “I wear a seven or eight long.” He also asked her for her shoe size as well as her underwear sizes. Shelby told him, although she was embarrassed by his direct personal questions.
Armed with the information, Sandy went shopping while Shelby worked the rest of her shift. Fortunately for the man, there was a mall just ten miles south of the Truck Stop in Woodlands.
When he returned, Shelby found out that he bought her a black evening dress, a pair of heels, and some very sexy underthings that included a very lacy racy bra and panty set, and some thigh high nylon stockings.
When Shelby was finally off shift, she ducked into the women’s restroom with a bag of clothing that Sandy had purchased for her. She peeled off her waitress dress along with her white bra and panties. She felt really weird standing naked in the employee bathroom of the truck stop.
She started to dress replacing her white utilitarian underwear with the new fancy lacy underthings. Next, she pulled the evening dress down over her head. As she pulled it into place around her body, she was amazed on how well it fit her. Looking in the mirror, the teenager thought she looked fantastic.
She was able to zip the dress up all the way by herself; she was pretty nimble even beyond that of a normal teen. Finally, she put on the stockings and heels, and after touching up her make-up, she was ready to go.
Shelby put her regular clothes into one of the bags the new items had come in. Double checking to make sure she had everything, she stepped out into the lobby where the man, Sandy, was waiting for her.
Before leaving Shelby said, “Let’s go to the office where I can photocopy your driver’s license and car registration. It’s upstairs.” Making their way up the stairs, Sandy handed over his documents, of which the girl quickly made copies.
As they were leaving, Shelby dropped the sheet of copy paper off with Liza down inside the restaurant. She told her acquaintance, “If I’m not here for my shift tomorrow evening, call the police and give them this.”
Liza grinned knowingly as Shelby, dressed in her long, black evening dress, walked out of the restaurant.
Shelby was a bit hesitant when Sandy politely held the door of a 2011 BMW 428i open for her. Taking a calming breath, she climbed in spotless car. Sandy walked around the front of the vehicle and got in the Driver’s side. Starting up the fancy car, it wasn’t long before the two of them were cruising down I-45 heading for Houston.
Shelby wasn’t worried about her dad finding her missing from home. He was working the entire weekend and would be stayed in the city until his string of shifts was over. The hotel allowed him to stay in unsold rooms for free so it wouldn’t cost him to remain in the city. He wasn’t due home until Monday.
Sandy rolled up to the Houston Hilton, and Shelby waited in the car as he went inside to check in. Shelby was relieved the man wasn’t staying in the hotel where her dad working, she was nervous enough without having to worry about bumping into her daddy.
Eric, Shelby’s father, worked as a concierge at the Hyatt Regency Hotel in Houston’s downtown district. Like all Hyatt’s, it was priced for business travelers and higher end vacationers. At $325 a night, it wasn’t priced for your run of the mill traveler or worker.
Eric loved his job, and with the investments he made with his wife’s life insurance, what had been left after buying the modest house, Shelby and he lived a pretty ordinary middle class lifestyle. The majority of Eric’s income came from tips; his $14.00 an hour salary was at the top of the salary range for a concierge, but his hourly wage was only a portion of his total income.
With the tips he received based on his vast knowledge of Houston’s nightlife, its underground, and its tourist locations, Eric made closer to $25.00 an hour. His large tips came from his ability to find obscure things or information for the Hotel guests.
He knew of things that ranged from the unusual to the risqué. He could tell you where in the vast city you could find the best meals or entertainment to meet anyone’s tastes; his knowledge was such that it included steering a man, or woman on occasion, to the best young women available for whatever budget you were constrained by.
Still, when related to a professional salary or even the pay for skilled labor, Eric’s annual income wouldn’t be considered very high. It was the returns from investments, which provided an additional $23,000 annually, and a house paid off that allowed Shelby and him to live in relative middle class comfort.
Shelby waited in the BMW checking her emails and text messages while Sandy registered inside his hotel, when he came out several minutes later, the man and his young date headed for dinner. Sandy asked her, “Do you like Cajun?”
Shelby giggled as she responded, “I don’t know too many Texans who don’t.” Based on Shelby’s response, Sandy took them to the French Quarter Cajun Seafood restaurant.
After dinner, Sandy asked the blond girl, “Would you like to see a movie?”
Shelby smiled and said, “Yeah, could we go see ‘Vampire Academy’, it looks wicked cool.”
Sandy smiled and said, “Okay, ‘Vampire Academy’ it is.”
Sandy thought the movie was just another silly vampire movie. But, it was what Shelby wanted to see. He had to remind himself that the tall, blond girl was still for all practical purposed just a kid.
Surprisingly, Sandy seemed to enjoy the movie. It had been ages since he had been to a senseless movie like the one they watched; as goofy as it was, it was surprisingly entertaining. Once the movie let out, Sandy escorted Shelby to the car driving them back to his hotel. Pulling up to the entrance, he turned the BMW over to the Hotel Valet and Sandy led young Shelby inside.
Shelby went with the man as the couple took the elevator up to the 17th floor where Sandy’s suite was located. He let himself and the nervous sixteen year old into the room with his key card.
Shelby looked around at the room as they entered through the door. She thought to herself, ‘This room is rather small for the high prices that the Hilton demands for it. The rooms at the Hyatt Regency are bigger and nicer.’
For Shelby, this was a moment of truth. She agreed to the terms, but wondered nervously if she could she actually follow through with it. If she wanted to back out, would Sandy allow her too?
Then again, she thought about how long she would have to work at the truck stop restaurant to accumulate the same amount of money; the total she would receive for just the one night. It would take her at least three months working steady shifts at the restaurant to earn the kind of money she was going to receive for spending less than twelve hours with Sandy.
Shelby would be paid to stay overnight where a good deal of it would be spent sleeping, at least she hoped she would get some sleep; she had no idea how randy her customer was. The fact that she was just minutes away from prostituting herself was just beginning to set in.
Shelby decided she was as ready as she was going to be, she had heard that doing it for the first time hurt like a bitch, so she was trying to brace herself for the event. She was pretty sure that Sandy was going to be gentle with her as he busted her cherry. She had been with the man all evening, and he seemed like a perfect gentlemen. He even sat through the goofy movie with her to help her relax and deal with what was coming.
As she stepped into the room, she started to take off her dress, only Sandy stopped her, “Um, if you don’t mind, I would like to do that, when it’s time.”
Shelby shrugged her shoulders and said, “Okay, no problem.” Her hands were shaking as she brought them back around in front of her. She clasped them together so it wouldn’t be so obvious how nervous she was.
Sandy went to the wet bar and poured himself some scotch over a few ice cubes, he asked, “Can I fix you a drink?”
She giggled, “I’m way too young to be drinking.”
He smiled at her, “If you’re old enough to make love, you’re old enough to have a drink.”
There it was, the first time it was stated outright what Shelby was here for. Although it had been implied before during their negotiations, it hadn’t been stated outright. It was time to trust each other that neither of them was ‘the law’ waiting to spring a trap on the other. Of course, even if Sandy was ‘the law’, Shelby was sure she had a good case to plead entrapment.
Shelby giggled, “Okay, I’ll try some wine.”
Her dad had let her have some wine at home off and on; Shelby liked the taste of the fermented grapes. When she tried beer at a party she attended at a friend’s house, she didn’t like the taste at all. She had no idea what to ask for when it came to mixed drinks, so she asked, “Do you have any white wine?”
He looked through the refrigerator at the mini-bar and asked, “It looks like there is pinot noir, chardonnay, riesling, or a muscat?”
She heard of chardonnay, so she asked for it. He found a small bottle of it in the refrigerator and poured it out in a glass for her. He picked up his scotch and gave her the glass of wine. Sandy was hoping the wine would help put the obviously anxious girl at ease.
She sipped away at the glass of wine as Sandy sipped on his scotch. She noted it tasted better than the wine she imbibed at home. It must have been a better brand, or vintage as her dad called it.
They talked, and soon Shelby found herself at the bottom of the glass. Sandy asked, “Would you like another glass?”
Shelby nodded, “Yes, please.”
Sandy went back to dig through the refrigerator until he found her another small bottle of Chardonnay. He poured it into her glass for her. He said, “That should help you relax without making you drunk. I really don’t want you drunk; I hope we can make the experience as nice for you as possible, but I would like you fully engaged.”
By the end of the second glass, they chatted for a good half an hour. Between dinner and ‘cocktails’, Shelby had found out quite a bit about her evenings companion. He was a salesman who dealt in medical devices and equipment. He made a very good living at it. He had the entire Eastern Texas region for a company called Advanced Medical Imagery, or AMI.
He was married to his wife Ashley and they had two children, Todd and Tanner, ages nine and seven respectively. He loved his wife completely, but he found himself being out on the road a lot, and he was indeed lonely for female companionship.
He didn’t consider it cheating as long as he gave his wife everything she needed, and as long as he didn’t fall in love with his ‘other’ girls. He never let his indulgences interfere with his sex life at home.
He had a couple girls that he met up with, usually one in each different city; he never let it affect his performance with his wife.
He was currently looking for a steady girl in the Houston area, hence his proposal to Shelby. Stephanie, his regular girl for the last three years, moved to Seattle when she graduated from College. So while in Houston, he needed to find a new ‘steady date’.
He liked his girls young--in the 16 to 20 year old range. At 23, Stephanie had aged out of that range, although he still enjoyed spending time with the dark haired girl.
He knew he was really pressing things by satisfying his needs with girls younger than eighteen. He knew that if he got busted for doing it with a sixteen year old or older that it would only end up being a misdemeanor. He paid the girls well enough they were happy to keep their mouths shut.
After he finished his second scotch, he moved over onto the sofa with Shelby and took her by the hands. He smiled at her and asked, “Do you mind if I kiss you?”
Shelby knew he didn’t need to ask, but she was pleasantly surprised that he did. She told him, “Yeah, sure, okay.”
He moved his mouth to hers and brushed her lips lightly with his own. She felt a tremor of pleasure travel through her body as he did. She found herself anticipating what was to come more than she would have ever suspected. His lips found hers a second time, only this time Sandy lingered longer, opening his mouth and letting his lips rub against hers as he began moving his lips around her mouth.
Shelby found herself responding in kind. She might have been a virgin, but she had experience with numerous kissing expeditions in the hallway of her school; Shelby was no stranger when it came to snogging.
Soon, they had their arms wrapped around each other as began to kiss fervently. Shelby could feel a fluttery feeling down inside her tummy as they kissed more passionately as the minutes ticked past.
Shelby enjoyed Sandy’s hands running up and down her sides and back as they kissed. It felt so sensual to the girl, the feel of his warm hands tracing up and down her body.
Then she felt him take the zipper on her evening dress as he slowly lowered it baring her back clear down to the top of her bum. Shelby was feeling her ardor build from the kissing and stroking, so when he went to remove her dress, she was more than ready to shrug it off her shoulders. As it came off her shoulders and down her arms, it slipped down her body to the floor where she simply stepped out of it.
Just that afternoon, if someone would have suggested that Shelby would be in a hotel with a man she had just met, standing in her bra and panties, lacy ones at that, she would have told them they were crazy. Yet, here she was. Sandy’s hands now stroking her bare skin the same way he had been doing it through the dress just seconds before. Shelby trembled at his touch.
Sandy reached down and let his hands roam over her panty clad butt. Again, Shelby shivered at the touch, reacting from it being the first time that a member of the other sex had touched her there sexually. She was astonished by how pleasurable it was, how aroused it was making her feel.
Sandy let his hands slide inside the waist band of her panties as he kneaded her firm, warm cheeks directly--hands on skin. Shelby made a mewling sound as tremors of delight radiated out from her core. She could feel herself getting steadily moister between her legs as his massaging hand gripped her ass.
Then Sandy’s other hand came up and found its way to her ‘B’ cup sized breast. He massaged her through her lacy bra, and Shelby felt her nipples get hard. She could also feel her body break out in goose bumps. She moaned into his mouth as he continued kissing her.
He broke the kiss and started kissing her neck, her ears and under her chin. Each contact caused her to tremble more and more often with pleasure. She delighted in the feeling of coolness between her legs caused by evaporation. Moisture from her pussy was soaking the cloth of her panties down between her legs.
Almost as soon as he started to kiss her neck and shoulders, he unbuttoned his shirt and shrugged out of it. Shelby was amazed that she found herself helping him out of his clothing; she was eagerly anticipating the promise of things to come. Sandy pulled his tee shirt up over his head, only missing a couple seconds of kissing her skin.
As he continued to plant kisses on her neck and shoulders, he reached behind her back and expertly pulled the clasps of her bra apart; her brand new lacy bra pulled away from her titties. Shelby shrugged the lacy garment off her shoulders letting it drop down her arms as it fell to the floor.
He quickly put his hands on her naked globes directly. He began to massage them lightly with his whole hand. He bent down and took one of her nipples inside his lips and he began to suckle. He alternated between sucking on the pebble hard nipple and flicking it with his tongue.
Shelby gasped out, “Oh, OH! Um, ah, um, ah that feels REALLY good!” She was feeling a myriad of new sensations she had never experience of before.
Shelby was a little alarmed when Sandy unclasped and unzipped his slacks tugging them down until they dropped to the floor. For the girl, it was one step closer to the culmination of their agreement.
He stood in front of Shelby in a pair of boxer shorts. She was down to her stockings and the pair of lacy racy panties. She knew there wasn’t much the lacy fabric was hiding; most of her secret places were visible through the lace and thin fabric, especially now that the strip of cloth under her bottom was soaked from her wet pussy.
Even though she was feeling really aroused from his mouth and hands, Shelby was still pretty nervous from what she knew was coming. She felt her desire climb; she felt the steady pressure building inside her vagina. But, again, she heard over time how much it hurt to have ones virginity taken.
Shelby wasn’t a stranger to masturbation; she had done it just that afternoon. She had been doing it for several years now, sometimes a couple times a day when she was really horny. Over time, she had many orgasms to show for it. But, she never found a need to go beyond the barrier just inside her vaginal opening; she never went beyond the small membrane barring access to the inner secrets.
At times she wished she would have broken the thing long ago, it would have been really nice to use tampons instead of pads during her periods. Plus, there were just times where she wished she could shove her fingers up inside herself when she was feeling the passion overcome her as she rubbed her clitoris. But, she was pretty much a coward; she was afraid of the pain it would have caused. Now, fear or not, it was going to be taken out.
Sandy took his time loving her breasts, enjoying first one then the other. Shelby moaned with desire as she continued to baste her panties with secretions from her vagina. Whether or not she was ready emotionally for a good fucking, her pussy was screaming for it, even though Sandy hadn’t even touched her pussy yet.
She didn’t have long to wait. He continued massaging one of her breasts as he sucked on the other. Taking his other hand that had been down inside her panties massaging her butt cheeks, he moved it around and for the first time, a man’s hand found her hot, wet vulva.
He cupped her pussy with his broad hand, she could feel his fingers tickling up against her vaginal opening and maybe a little further back onto her perineum; it was a fraction of an inch in front of her puckered brown anus. She moaned out in pleasure as his hand conformed to her anatomy.
He slid a finger up through her wet outer lips, pulling her labia apart, travelling up until the tip of it brushed over her swelling clitoris. She felt jolts of pleasure radiate up from deep inside her vagina out into her tummy and up though her body. It was almost as strong as one of her orgasms produced by her fingers while masturbating. But, she knew that there was a stronger reactions to come, she could still feel the pressure building up inside.
He reached under her legs picking her up and he carried her to the bed at the other end of the suite. She snuggled up against his naked chest. She was both shivering in anticipation, and trembling from dread knowing what was soon to come.
He laid her down on her back, and began to make love her boobs again; his hand found its way back between her legs. He lightly stroked between her lips with a finger some more, only brushing her clit intermittently. It was enough to keep her desire at a peak without pushing her over the top.
Then Sandy started down her body planting wet, warm kisses on her chest and around her diaphragm. He was kissing and licking her all over, and each place he concentrated on seemed to cause Shelby to tremble in delight. Tremors radiated throughout her aroused body.
Shelby was anticipating that any moment, he would climb between her legs and she would cease being a girl; she would become a woman. Only, he just kept kissing down her body.
When he came to her lower tummy, she felt him pull down the waist band of her lacy racy panties. He followed the flimsy cloth down even further. The waist band of her panties kept moving down and so did his mouth.
With both hands, he grabbed the band over both of Shelby’s hips and he gently tugged on her panties. She lifted her butt just a little so they could slide past her bum and down her legs; the small cloth garment kept moving until they disappeared over her ankles. The only thing keeping her from being completely naked was the pair of dark nylon stocking she was wearing, held up by a garter on each thigh.
Shelby felt the man begin kissing her pubic hair. She had never felt anything so erotic before in all her life. He gently pulled her hair with his lips repeatedly with his lips, causing her tremble each time. She moaned loudly as she finally figured out what Sandy intended to do. It never occurred to her that he would want to put his mouth on her pussy.
She was already feeling her passion grow unbearably, but the idea of Sandy putting his mouth between her legs was pushing her to her peak. As Shelby got more aroused she got wetter between the legs as she anticipated Sandy’s next move.
Sandy moved between her legs, and she spread herself to welcome him in. She had never been in this position before, lying naked on a bed with someone between her spread legs. The closest thing to a sexual encounter she experienced before was when her best friend, Jessica and her masturbated together during a sleep over.
Shelby knew he was looking at her pussy, taking in her shape and form, studying her inner recesses. Instead of embarrassment, it added to her ardor.
She felt his mouth take in one of her pussy lips sucking on it. Shelby gasped as she felt her passion reach an unbelievable level from the contact. After Sandy sucked her lip from bottom to top, he sucked in her other fur covered lip giving it the same treatment. Again, she felt sparks of pleasure radiating through her whole being.
Then he split her cleft like Moses parting the red sea. His tongue slid into her vaginal opening and then he slowly wiggled it all the way up to her clitoris separating her labia the entire way. When his lips and tongue finally found her love button, he sucked it into his mouth and started to tease her with his tongue.
That was all it took, the incredible pressure inside of Shelby’s vagina released. Starting with sharp spasms inside her vaginal canal, it overtook her body like a starburst. Her opening began to contract spasmodically causing waves of delight to ripple both up and down through her body.
Shelby’s legs quivered and snapped open and closed; at times her thighs trapped Sandy’s head between them. Her tummy, then her chest, and then her whole body began to writhe in ecstasy. She had never felt such an explosion of pleasure, no matter how many times she had massaged her clit in the past.
This was new and pleasing to the point it was nearly painful. She gave herself over to it and let it wash through her entire being. For those many long seconds, life was an orgasm!
She started to calm after about fifteen seconds only Sandy didn’t stop. He found new places to explore, new things to do to her with his mouth. Within a minute of the first climax, Shelby was experiencing the strong throws of her climax all over again.
Shelby felt it as Sandy lapped up her copious secretions produced during her orgasms. He seemed to relish in the taste of her juices that he gathered with his tongue.
To get to Shelby’s nectar, Sandy pushed his tongue up inside her hole. He had his tongue buried clear up to her hymen gathering her delightful cum. He kept her rippling along in total orgasm for over a minute.
As Shelby shook in a frenzy from the last of her repeated climaxes, Sandy made his move. He quickly crawled up between her legs. His boxers were missing; he took off the last of his clothing while he caused Shelby to have her orgasms.
Shelby felt something both hard, and at the same time soft, pressing up against her bottom. She rocked her hips up in welcome as Sandy moved the head of his penis between her lips. He rubbed himself between her hot, wet lips preparing for action. Shelby was still so involved in her orgasm, she didn’t have the senses to be nervous or afraid; she was barely aware that her hymen was in imminent peril.
Within seconds of Sandy moving into position on top of the lovely blond girl, he pushed his cock into her vaginal opening; the head of it ran up against her barrier. He wanted to move quickly, to bust through it while she was still lost in her orgasm. He pushed a second time against the barrier with just a little more force causing it collapsed. As he felt it popped, he slid into the place where no man had gone before—deep inside of Shelby’s vagina.
Once he penetrated her barrier, he easily slid all the way inside her, burying his hard cock completely inside her taut belly. He heard her gasp out as her hymen gave way. He could feel her vagina snuggly wrap around his shaft, expanding to allow the barbarian invader though the gate.
Shelby felt a sting as her maidenhood buckled, but it wasn’t nearly as bad as she expected. She heard time after time that losing your virginity was supposed to really hurt; only when she felt the pop, it resulted in just a mild sting.
She presumed that maybe by the time she was sixteen she had stretched it out and it was just waiting to be broken by the slightest pressure. She moaned out, “Oh my gawd! Shit, that feels nice! Fuck me, don’t stop now! Fuck me!”
Sandy was delighted by her reaction; he didn’t need any more encouragement. He withdrew his cock a good three or four inches, and then he pushed back inside until he was snugged up against her pussy once again. Then he did it again and yet again until he had settled into a delightful rhythm that was pleasing to both of them.
Shelby was fucking. She never experienced anything like what she was feeling before. As Sandy pushed into her, she felt a delightful fullness, it made her feel complete. She could feel the flange on the head of his cock slide along the inner walls of her vagina. Millions of nerve endings fired off, sending her brain wave after wave of incredible pleasure.
Before long, Shelby felt herself start to tremble and then quake as yet another orgasm overflowed her senses like the tide. She felt it build, rising slowly to overwhelm her. She felt it release and then it slowly role out through her body as it subsided. It wasn’t the sharp, breathtaking orgasm that she got from clitoral stimulation, but it was just as nice.
After about three or four minutes of Sandy sliding his cock in and out of the young teen, he felt himself starting to tense up deep inside his bottom until it exploded from his balls. His testicles were sucked up tight against his shaft ready to deliver its heady brew. He crammed his full seven inch cock deep inside the girl as he let it explode inside her. Only then, had it occurred to him to ask the girl if she was on birth control.
Shelby could feel him tense, and then she felt a pulsing sensation as he pushed his hardness all the way up inside vagina. She felt his head push up against what she could only guess was her cervix as hot semen bathed it with each of his squirts. She felt so full and complete as he ejaculated spurt after spurt of cum up inside her tummy.
He moaned as he collapsed down on top of her, his head next to hers. He whispered, “Oh my gawd, girl! That felt fantastic. You’re so tight! I love your hot, wet pussy wrapped around my cock--my goodness, what a honey hole!”
She giggled, “Yeah, I liked fucking you too!” Then she just let the sensations flow over her, “Oh my gosh, there isn’t anything else like this in the whole world!”
He stayed inside her until he started to go limp. He finally fell out of her pussy and a bolus of comingled cum followed. He must have really filled her up, to have that much of it dripping out of her opening like that. A goodly amount of it was meant to go up through her cervix into her uterus to look for an ovum.
Shelby felt him slip out of her. She felt an emptiness once he was gone. It felt so wonderful to be filled by him, and it was almost a letdown as her vagina contracted back to its normal tight state.
He rolled down to her side and held her against him as he enjoyed the an afterglow after filling her virginal love canal with his cum.
She felt a large trickle of their mingling juices dripped out of her now open vagina; she felt it drip down over her tight little anus. The feeling of it sent a shiver of delight through her body; she loved how it tickled her other hole. Her senses were on high alert, and she was ready for more, she needed to feel him back inside her.
Shelby reached down and grabbed his slick, but now flaccid penis and started to play with it between her fingers. It took a bit, but he started to respond as she did. She wrapped her fingers around him and gently stroked him up and down the full length of his shaft until he was fully restored to his prior glory.
Shelby giggled again as she climbed up on top of him, she announced, “My turn!”
With her knees straddling his hips, she rose up and gently guided his stiff pole with her fingers back inside her opening, and then she sank down on him letting him fill her vagina again. She sat for several seconds, enjoying the feeling of his big cock stuffing her.
Shelby began to lift up and down on his shaft using her knees. She felt overjoyed as she felt of his large cock sliding against the length of her canal again. In addition, her clit was being squeezed each time their pubic bones came together. After several minutes, she was trembling, shaking and quaking all over again as another wonderful orgasm overtook her body.
As she came, Sandy rolled them over positioning Shelby on her back again. He pulled her down the bed and rolled her asking her to get on her knees at the edge of the mattress. Having her spread her legs apart a bit so she was at the right height, he slipped his long, hard shaft back inside her from behind.
Standing against her butt, he started to pound into her backside. The room was filled with sharp staccato sounds as hips slapped against her firm butt cheeks and thighs over and over again.
Along with the smacking sound, her juice filled vagina made slurping sounds with each thrust that provided counterpoint to the sharper smacking sound.
Shelby knew that she was addicted. From her very first time, she knew she was going to enjoy fucking whenever and wherever she could arrange it. She knew this was going to be her vice, her Achilles heel. She was going to be a slave to finding her next fix. Fucking would be her drug.
The sounds of their fucking was driving Shelby wild with lust. She knew that between them, they were a complete mess of juices and cum, her entire bottom and her upper thighs were coated with it.
She loved every second of Sandy pounding against her bottom. She could feel every thrust of his cock sliding deep within her tummy. The naughtiest part of it all though was she was being fucked by a complete stranger—for money. This just made it that much more erotic and arousing. Just thinking about the wickedness of it made her cum again.
Sandy repositioned her again as soon as she was coherent enough to move. He sat on the bed and pulled her into his lap with her facing him. Shelby pulled his cock into her pussy by reaching behind her butt. Once in place, she sat down, impaling herself once again on his hard shaft. She held her head against his as she controlled the rhythmic penetrations.
She loved it most when they were conjoined bone to bone, with Sandy deep inside her tummy. She also loved feeling the man’s skin as her whole body rubbed up against him as she raised and lowered herself. She especially loved the feeling as her hard nipples rubbing up against his warm chest as she rode his cock.
Sandy loved fucking in this position too; he was able to hold the tall, beautiful, blond girl tucked in close to him as she wrapped his cock snugly within her tight pussy. Sitting in his lap the way she was, she was actual just a bit taller than him. It made it easy for him to start kissing the girl again as they fucked.
She seemed to have orgasm after orgasm as she experienced intercourse for the first time. Sandy gripped her tight butt cheeks as she rose and fell onto him repeatedly.
After fucking him while sitting in his lap for a good five or six minutes, he could feel her pussy convulse around his shaft as she began to quake uncontrollably yet again. This time, he could feel her entire orgasm as she wrapped her arms around his neck and squeezed him tight as it overwhelmed her. He listened contently as she vocalized her pleasure right next to his ear.
Already feeling his own climax build, her delightful orgasm was the catalyst for his own. He shot his load deep inside her belly for the second time that evening. The pulses were strong and radiated up through his back and down through his thighs. He could hardly remember a time when he came so hard. This blond firebrand was an incredible fuck as well as an enjoyable companion. Recreational sex rarely got better than this.
As the couple came off their joint climax, the two of them melted onto the bed. Sandy pulled the spent girl into his arms and held her close. He kissed her neck and ears as he told her how nice the whole experience had been for him. She just purred and wiggled her naked butt back up against him. They both fell asleep with Sandy spooned up against her back and bottom.
Sometime in the middle of the night, Sandy dreaming of something sexy awoke just as Shelby pushed him over onto his back so she could straddle his hips. She impaled herself once again on his hard shaft. She rode him for a couple more orgasms on her part, and then she just sat on him grinding her hips around him until he cut loose with another hard climax. Both of them drifted back off to sleep.
Near dawn, Sandy awoke again with another raging hard-on. He quietly slipped it between the girl’s legs from behind pushing himself neatly up inside her vagina. She slowly woke up with his slow methodical fucking. She giggled, “Now that’s the way for a girl to wake up!” She laid on her side and let Sandy do all the work; she enjoyed the feel of his hard softness gliding up and down through her canal.
After they both got off yet again. They lay together for a while enjoying the afterglow. The agreement had been fulfilled and they both had places to be that day. So after a bit, they got up and showered together.
After dressing, Sandy drove Shelby 45 minutes back to Conroe. He told her that she could keep the dress and other accoutrements, and that she more than earned them.
On the way, Sandy stopped off at a Bank of Texas branch and made a cash withdrawal of $3000 from his bank account. He handed Shelby the wad of cash with a smile. He said, “You were expensive, but worth every dime. Can we get together again?”
Shelby smiled and asked, “You said you would spring for $600 for a nice evening?”
He laughed, “Yes, I guess I did, didn’t I. You’ve turned into quite the business woman.”
She grimaced as she said, “I guess the term would be quite the prostitute.”
Sandy smiled at her, “Why don’t you say, ‘quite the courtesan.’ I think it fits better.”
Shelby asked him, “So, when should I expect your next, um, visit?”
He responded, “I’ll be back through in two or three weeks. I’ll give you a call if you’ll give me your number.” So she gave him her cell phone number and he added it to his contacts list in his own phone.
Then he asked, “Are you interested in other, um, companions?”
She didn’t commit, she asked him, “Why do you ask?”
He smiled and said, “Well, I have quite a few friends that would be interested in an interlude with a young woman like yourself. They are looking for a young woman they could have a good time with, and better yet, someone they could trust not to be a sting operation. I will personally vouch for anyone who I send your way. They will be trustworthy, and more importantly they will be disease free.”
Just the mention of STDs made the whole idea of fucking for money less palatable to Shelby, but at $600 an evening. She was still interested. Then she decided to test the waters. She asked, “So, what do you think $600 should buy?”
He responded as he passed a semi-truck, “Well, for a high priced call girl. I would expect to pay $400 to $600 for an hour or two. Most guys can get what they need in an hour, unless they are feeling really randy. I would charge at least a thousand to spend the night I were you. Keeping the price high will help you weed out many of the undesirables.”
She thought about it and was quiet for several minutes listening to the road noise as the BMW approached the outskirts of Conroe. She finally said, “Why don’t you refer one or two ‘gentlemen’ to me and I’ll see if it’s going to work out.”
He replied, “Okay that sounds like a good idea. If you want more you can let me know the next time we get together.”
Then he hemmed and hawed a bit before telling her, “Um, Shelby, a lot of us ‘customers’ will probably want a, um, want oral sex as part of the package. Are you going to have any problem with that?”
She thought to herself, ‘Oh, yuck! I never thought about that. Can I actually do THAT? Eeewww.’ Responding to his question, “I don’t know, maybe. I think so. But I won’t know until I try it I guess.”
He said, “Well, I guess that if you wanted to leave it off the table, you could charge less. Although a few of the guys I know would pass all together if it wasn’t included.”
She repeated, “I’ll think about it. Giving a blowjob seems a bit demeaning to me.”
He agreed that to give a stranger a blowjob might seem that way, but most of the guys he would refer to her would be regulars and she would get to know them, then it probably wouldn’t be so bad.
Then he mentioned, “Do you have a problem if the first guy I refer to you is a little overweight? Not like morbidly obese or anything, but he has a bit of a ponch.”
She hedged, “What’s he like?”
He said, “Well, he’s a really nice guy and from everything I know about him, he sounds like he would be really gentle with the ladies. He’s got a real problem at home that I’m not at liberty to discuss, but Terrance Jacobson would really be a nice follow-up if you ask me. The nicest thing is that I think you could get away with not giving him a blowjob if you are still having issues with it.”
Shelby smiled, “That’s a plus, I guess.”
He turned to her and said, “Something you’re going to have to get used to Shelby is that these guys aren’t the football jock types. They are regular guys and they all have their warts. They wouldn’t be looking for paid company if they were all prince charming.
“The men I refer your way will be nice guys, but there will be no guarantee that they will be the best looking guys. Some might be bald, other’s a bit overweight, and still others may be homely. What you can expect though from anyone I send your way is that you’ll be safe with each and every one of them, and that each of them will appreciate what you have to offer.”
She smiled and said, “Okay, let me meet Terrance, and we’ll see how it goes from there.”
About then, Sandy pulled into the parking lot of the McIntire Truck Stop and let Shelby out. As an afterthought, she motioned for him to roll down his window and when he did, she gave him a lingering kiss goodbye.
She grinned and said, “See you next time, Sandy.” She skipped away happily looking the part of a sixteen year old girl who was completely contented. He watched her as she headed to get her bicycle so she could ride it home.