Chastity's Road to Fulfilment

Chastity looked in the mirror. She was wearing her dark blue prom dress that still set off her blonde hair even though she graduated two years ago. It fit beautifully and she enjoyed the way the satiny smoothness fell just right over her 21 year old thighs. In fact, the dress looked better now that her curves had ripened and her face had lost its baby softness.

She was going on a date with her boyfriend Donald to a fancy restaurant. So fancy it was an hour out of town and she had only heard of it through affluent friends.

She had expected this night to come for a while. Donald had just finished up his associates degree at the local community college, landed what he thought of as a "decent" job and she expected a marriage proposal soon. In fact, tonight might be the night he got on his knees and popped the question.

There was only one problem. Donald was handsome and polite, and nice to her parents who thought the world of him. He cared about her, and she was even certain that he loved her, it was just that...well, they had never had sex. Despite the fact that they had been going together for four years, they had never done the deed. Not even once.

Of course she was sure everyone (including her family) thought they were fucking like rabbits. It certainly would stand to reason, and she did feel like he was attracted to her. She could feel him looking at her with lust in his eyes, and there was a magnetism there that was obvious to everyone who met them.

In fact, her mother had given her a long talk back when she started dating Donald. She went on about using protection and not letting her hormones compromise her morals, but she had never so much as seen his cock. He kissed her all the time, felt her up, and once he had even seen her breasts without a bra on, and she had rubbed up against his hard cock, but he always stopped short of taking it out of his pants.

When she brought it up, he said it was because of his religion. He went to church and was a good southern Baptist, so he felt a man and woman should be married before they had intimate contact. After all, his father was a deacon who took the job very seriously, and his mother a Sunday school teacher. He had been raised in a family where you went to church on Sunday, and abided by biblical teachings in all situations. Sex before marriage was just not something done in their family.

Chastity was religious too, to a point, but nothing like Donald. She believed in keeping up with the times, and that the views presented in the Bible, especially those presented about sex, were outdated. The Bible was a great tool of course, but was very much written at a time when there was no such thing as birth control, and women could get pregnant easily. They didn't have condoms, diaphragms or the pill back then. There were no reliable ways to keep from getting pregnant or diseased, so it was forbidden. Now a days if consenting adults wanted to have sex, they should be able to.

The sex talk was the only disagreement they'd ever had, if it could really be called that. She wanted to try sex before marriage, but he didn't, so they continued to kiss and fondle each other, never actually consummating in the actual act. She felt almost depressed that here she was, already 21 years old, naturally blonde, tall, athletic and trim, and yet she was still a virgin.

She saw Donald's headlights outside her apartment window, and her phone lit up with a text saying "I'm here!"

She didn't see any point in making him come up, so she replied "Be down in a second", grabbed her purse, headed out the door and down the stairs of her rustic building.

It was a long drive to Pascal's, the restaurant they would be going to and they didn't talk much on the way, opting to listen to music instead. Once there though, they were greeted by a man in a tuxedo and led into a candle lit room with linen napkins, silver salt and pepper shakers and handed simple sheets of paper with neat cursive font on them for menus. It was the type of place where everything was a la carte, and when the waiter spoke, he did so with a faint European accent.

"Wow, this is great," Chastity told Donald, enjoying the faint tinkle of piano keys coming from somewhere in the next room. She had only ever been to "nice-ish" restaurants in Oak Falls a few times a year, and this one was over and above any of the places she had been to with glass on the tabletops for easy cleaning and wipe off-able menus.

They talked about Chastity's secretarial job at the hospital and the new job Donald had just landed now that his associates had finished. He had quit his job at the grocery store only a few weeks before, and was now an assistant in the accounting department at a large law firm. He didn't love the work, but saw potential to rise up the ladder and the salary was more than enough to allow him to save up for a while and put a down payment on a house.

Eventually over dessert he said, "Well, I've brought you here to ask you something, and I hope you'll be happy about it." Chastity got excited. This was it. He was going to ask her to marry him. She smiled. Had he told her parents? Did her mother know?

"Yes?" she said expectantly.

"Will you have sex with me?" he asked and cocked an eyebrow.

"What?" Chastity said, slightly disappointed.

"I just got to thinking about what you said. Maybe it's best we do it before marriage."

Of course she had said as much herself, but hearing him articulate the thought in a high class restaurant where people came to celebrate milestones and well, actually get engaged was unromantic and tacky. You didn't bring your girlfriend to a place where they used real bone china and silver then ask her to sleep with you.

She took a deep breath, trying not to look too upset. "I told you I wanted to. It seems silly not to at least know if we are compatible that way or not." She was trying now to sound practical.

He brightened, oblivious to his tactlessness. "Oh that's great news. I booked a room for the night. That is if you're still up for it. I even got some...you know." he said, and she assumed he meant condoms. He was probably the only man in the western world who would blush at such a thing. Well, she wanted to do it and he was finally willing, so she would. She was ready to be devirginized and understand what all the fuss was about with sex.

After the bill was paid and they made their way to the hotel, Chastity found she was a bit nervous. It must have cost a fortune to rent the room. It had a king sized bed and hardwood floors. There was a jacuzzi tub in the bathroom and a large shower stall with so many settings she couldn't begin to operate it. It even seemed as though the floor could be temperature controlled, though neither she or Donald tried to figure out how to do it.

She took a long bath to relax, and once out, Donald was already splayed on the bed in his tighty whities. She had seen him in a bathing suit before, so it wasn't a shock. He was a good looking guy. Not in as good a shape as he had been in high school, but he was still the cute boy who had been on the wrestling team, the boy she had been wildly in love with in high school.

She felt a little put out that Donald didn't give her any warning about the trip. She didn't have a change of clothes or shampoo or any toiletries. She did use the toothbrush Donald had brought to brush her teeth, but otherwise her skin felt dry from the gross hotel soap she had used and she was only wearing a towel when she came out of the bathroom and would have to sleep naked.

She looked at Donald, who seemed to be looking everywhere but at her, took off the towel, threw it on a chair and slipped under the covers.

"Ok, so what do we do here?" Donald asked when she was safely shrouded in blankets.

"Well, you put your um..." she said.

"Yeah, I know. Penis in the vagina." he said awkwardly

"Ok, so um..." she said and tried to kiss him, but he didn't seem to want to so she went right for his crotch, and found him to be limp. "Let's turn out the lights, ok?" she said, thinking he might be nervous and his cock might spring to life when he could no longer see her.

"Yeah." he agreed, turned the lamp off and turned back towards her.

This was not the first time Chastity wanted it to be. She felt like crying. Sex was supposed to be passionate, and she wanted to feel like he wanted her. He didn't seem to crave passion at all. He barely ever even wanted to cuddle. Still, she was determined. She wanted to have sex. She wanted to know what it felt like to bond with another person and be gripped by passion like every other adult seemed to have experienced. She wanted to know what it felt like to cum with another person, not just with a dildo or her hand. She loved Donald. Truly. He was a great guy except for this one thing.

"Just relax." She coached, wondering why she had to be the one to talk him into it and started tenderly touching his cock like she had seen in the porn movies she watched on occasion when her desire for sex reached a fever pitch.

Finally, Donald's cock got hard enough to put a condom on, and in the very dim light, only from the glittering outside view of the city, he reached over to the bedside table, grabbed a condom and slid it down over his dick. Chastity allowed him to climb on top of her, and he tried to put it in missionary style, but she wasn't really wet. She almost suggested that he go down on her, but then thought it would result in more delays, and possibly his cock going limp again, so instead she tried to help him by maneuvering her legs so that her hole was more accessible.

After several moments, Donald's dick finally went inside her. It hurt a little, and he thrust a few times. She thought of saying something to help him along, but decided to remain silent since she wasn't really enjoying it. After a few minutes, he pulled out. She was sure he hadn't cum and she hadn't even approached being turned on.

"Did you like it?" he asked, and Chastity sighed heavily.

"Yeah." she lied, though it hadn't been anything like what she had seen in porn and read about online. Sex was supposed to be exciting, and she was supposed to reach a climax. She masterbated fairly regularly. Much more now that she wasn't living at home with her parents, and had even popped her cherry with a dildo out of curiosity. That had been far more satisfying. If this was real sex, she would stick to pleasing herself. It was the biggest disappointment she could have imagined. He didn't even kiss her.

"Ok, well. Let's go to sleep." Donald said, plucked the basically unused condom off his cock, threw it in the trash and turned over on his side. Later he left the room and paced the halls.

..............................

On the way home, Chastity didn't say anything much, and when Donald dropped her off at her apartment in the morning, she felt stupid wearing her prom dress and heels in the glare of midday. She was glad she didn't see anybody on her quick walk up to the second floor.

That night she had a long talk with Donald, and told him she wanted to take a break. That she needed some time to think about things, and wasn't sure she was ready for marriage. That she loved him, but he had been her only boyfriend, and she wanted to be alone for a while.

He was upset. He told her it was the stress of the new job, that he had been nervous, and he was sorry he hadn't been able to deliver in the bedroom, but agreed they should take some time to reflect on what happened.

Two weeks later, Chastity was eating lunch alone in the dining hall at the hospital when a handsome man with dark hair appeared at the table where she was seated alone. He was in great shape, tall, tan, and his nametag read "Doctor Robert Cloud." She almost thought it must be a joke since he was in fact, so dreamy. The type of guy who would play a doctor in the movies, not actually be one.

"This seat taken?" he asked as if he were doing her a huge favor. He smiled revealing white even teeth, as though he were used to having women swoon all over him.

"No, please. Sit" she said, happy he had chosen to sit next to her, even though there were lots of empty tables around. Lots of smart doctors and administrators to sit with too who would be much more interesting than she was. She didn't do anything but file papers, manage calendars, book flights and answer phones for the researchers.

"So how do you like St. Jude?" he asked as though she were some kind of new recruit.

"I like it fine." she answered. "I work for the research group one flight up. Just keeping them organized I guess."

"Hmm, that's probably why we haven't met," he responded. "I'm a pathologist, so I'm usually in the lab working upstairs. I'm only here filling in for a while so I haven't met everybody. Most of the time I go out for lunch or eat at the kiosk by the giftshop."

She didn't really know what to say, but he wasn't phased by the lack of conversation on her part. Instead kept up a steady stream of questions about her background. At first she didn't say much and only gave one word answers, but he was so easy to talk to after awhile she found herself telling him in detail about what high school she attended, how she felt about the new hospital director and if she knew any good restaurants to go to. At the end, he had made her feel comfortable enough to ask where he was from. She found out he had come from somewhere in Colorado, was recently divorced, had two kids, and would be leaving soon to go back out west where he was permanently based to spend time with his kids.

"And that's my pager." he said, "Could we continue our conversation over dinner?" he asked.

Chastity was surprised he would want to go out with someone like her. He was so charismatic and charming and handsome. Far too accomplished for a girl of 21 who had never lived outside of Oak Falls. Still, she found herself enthusiastically nodding and giving him her phone number.

"Alright then. I get off at 6 today. I'll give you a call and we'll go to that place you were talking about. Renaldo's."

She was skeptical he would remember her at all. In fact, she imagined he would find the number several months from now, think, who is this? Draw a blank and delete it.

The day drug on, and shortly after 6:00, to her utter amazement, he did call. She was thrilled. "I'll pick you up at 7:30" he said, and she enthusiastically showered, put on a black skirt, dress shoes with a modest heel, and a lacy black and white shirt that drew attention to her breasts with no bra since her breasts hardly required it. Then, almost as an afterthought, even though it was only Tuesday, she put her panties and a travel sized toothbrush and toothpaste in a plastic bag and stuffed it in her purse. Just in case.

She met him down at the parking lot, not wanting to have him up to her apartment since it was so modest, and they sped off to Renaldo's in his Tesla, which was the newest most up to date car Chastity had ever been in. It had heated seats, and he laughed when she gasped and he took his hands off the wheel to look her full in the face while driving at 60 miles per hour. "It's on autopilot." He explained, "The car drives itself."

"Well, take it off, it freaks me out." she said. He did, but chuckled at her distrust in technology.

At the restaurant, while she found him just as easy to talk to as she had at lunch, she got the feeling he would have been more at ease at dining at Pascal's where she had gone with Donald a few weeks before. Even so, he was nice about it, and acted as though her choice of restaurants was superb.

When he asked why she hadn't gone to college, she lied and said wanted to stay in Oak Falls because her parents were elderly and needed her help. Not the truth, which was that she had never been much of a student in school, had been held back in school, and though she was a lot better at learning now that she was older, she was sure her teachers would describe her as more average than stellar. Also that she had anticipated marrying Donald who she did still love and miss, but was unsure about now.

At the conclusion of the meal, before he turned on the car, he said "you want to come to my place? There's a hot tub."

"Oh. Well, I don't have my bathing suit with me." she stammered, wanting to go, but not sure if he somehow expected her to have a bikini on under her skirt and shirt.

"You won't need it." he said and leaned over to kiss her.

The kiss wasn't anything like she ever experienced with Donald. Robert was magnetic. He was so in control and seemed to know exactly how to please her. He didn't ask permission and wasn't hesitant. She enjoyed his tongue darting ever so slightly in her mouth, enough to tease and entice her, and her heart started beating in anticipation of what it might be like to be close to this man. To feel his hard body on top of hers thrusting.

She knew he wasn't after a relationship. After all, he had been candid enough in saying he would be going back to Colorado at the end of the week. She should probably be a good girl and ask him to take her back to her apartment so she could enjoy a long bath in her own bathtub, but she made up her mind when she put those panties in her purse. It would be a one night thing. He had pretty much come out and said so. He wanted to fuck her. Pure and simple. She could take it or leave it.

He stopped kissing her and looked at her expectantly.

She decided she would take it. She was already 21 years old and had yet to experience what her friends in college seemed to do all the time. There weren't any handsome frat boys riding up in Chevy Yukon's wanting to take her back to their beer soaked houses in Oak Falls. This was her chance to live a little. Have a little excitement in her life, and with a rich doctor instead of a smelly frat boy. This man was hot, and likely knew his way around the bedroom.

"Sounds like fun!" she said impulsively, and she felt her pussy throb in anticipation of feeling this man, all of him against her.

When they drove the short distance to his house, she saw it was massive, and in an area of town she rarely visited and full of wealthy people. He explained it was a rental, but why he needed such a big place for just one person boggled her mind. It was a sprawling ranch with a three car garage, and so many amenities in the kitchen she wouldn't have known how to begin to cook a meal in there. He even had a wine fridge, which she had never even heard of, and she listened to his explanation about how it kept it at the perfect temperature and humidity.

He then pulled out two glasses and a bottle of what he said was Chateau Lafite. He filled the two glasses about two thirds of the way full and took her out to the large pool, then under a cabana in a corner where there was a jacuzzi tucked into the corner. It looked like there were towels already stacked in a cabinet.

"See, nice and private." he said, handing her a glass. He then pushed a button that caused the tub to roar to life and began to strip down to his boxers.

Chastity realized he was in amazing shape in a way she hadn't appreciated with his clothing on. He was at least 35 if not a little older, and had a perfect V shape torso. She realized she was a little in awe of him. He was tall, tan, and muscular, and smart, and she watched him ease his way into the water, then take a sip of his wine.

"Come on in, it's great." he said as she just stood there on the polished stone not knowing what to do. "I promise I won't bite." he paused "well, without the intent of pleasure anyway." he said, and laughed. When she didn't react, he said "Just kidding. We don't have to do anything you don't want to. I promise. Come on in"

Oh but she did want to. She knew so many girls would kill for the opportunity to be with this man in this house that was better suited to royalty than a mere mortal like she was. Chastity took a big gulp of wine. It tasted bubbly and sweet, yet somewhat unpleasant. She hoped it would relax her and then took another one before setting it down.