Lucky at Last
Mar 4, 2023 // By:analsex // No Comment
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There are those people who are lucky at cards. Some are lucky in business. Many people are lucky in the game of love. Christopher John Tyler was not one of those people. Love had eluded him and when he did think that he’d found it, he got slapped in the fact — twice.
He had a good job from the time he was 15 and worked as many shifts after school as he could. He made sure to maintain his grades so he wouldn’t have issues with his parents. By the time he was 17, he owned his own car when many of his friends were still riding the bus. Despite all of this, the girls still didn’t flock to him. He got some dates, but many of those girls just wanted to go somewhere and do something, and he had a car. After a while, he got sick of being used for a ride and a free meal.
Chris finally thought he got lucky in his early 20’s. A mutual friend introduced him to Lisa Lynn. For Chris, it was love at first sight, and why not? She was everything that Chris liked — tall, blonde and a bit quirky. He never could understand why, but quirky had always appealed to him. He also liked her crooked smile and great legs. She wasn’t afraid to show off her body and with a job in fashion, she dressed well. It did Chris’ ego a lot of good to be seen with her. The book store he had opened was making a lot of money, so he now had it to spend. As far as Chris knew, he had found the one.
Only he hadn’t and when reality came around, it was going to hit him like a concrete pylon.
About a year into their relationship, it finally happened. He had never pushed Lisa into having a sexual encounter because it wasn’t the crux of their relationship to him. He loved her companion and, as far as Chris was concerned, the fact that they loved each other was at the very heart of things. He had bounced the idea of marriage off of her and she had parried some of his thrusts. She told him she would have to think about it and assured him that they wanted the same things. Being in his 20’s, Chris didn’t push. He knew that they had time. His bookstore was one of the best in town and he was getting a sterling reputation for quality merchandise and fair business practices. Business was up by 25%, so he thought about buying her an engagement ring. Then, Chris made his first big mistake. He mentioned it to the friend who had introduced him to Lisa. The well-intentioned friend, knowing Lisa did not want to get married yet, intervened. At first, it seemed like the intervention went in Chris’ favor.
Lisa seduced him one night while they were at his apartment. As far as he knew, her sexual history was little or none. His own was none, although he knew more than most men from all the reading he did. His girlfriend came over for dinner and stayed for breakfast.
Poor, hapless, naïve Chris truly had no idea how devious his girlfriend was. He knew from the minute she walked out of his bedroom in a black negligee and black heels that he was being seduced. He didn’t mind, he wasn’t opposed at all to their relationship becoming sexual. She was quite — enthusiastic — in bed and she gave amazing head, or at least, Chris thought she did. He had no basis for comparison. All he could say by the time it was over was he could have let her do that for hours and been a very, very happy young man. She was even naughty enough to swallow, which fascinated the soon-to-be ex virgin.
Chris was not a perfect physical specimen, but Lisa made it clear to him that besides his being a nice guy, he had a pretty nice cock. She splayed out on his bed like Aphrodite or Venus and demanded her just rewards. Chris had read enough books and seen enough porn to know what to do. He thought he knew where to kiss, what to touch and where to lick. If not, Lisa was a smart young woman, she would tell him.
He had never noticed until he slowly undressed her black lingerie-clad body, but his girlfriend must have worn very little when she tanned. The tufts of fur above her pussy confirmed his theory that Lisa was not as blonde as she would have had him believe, but he didn’t care. He loved the woman, not the hair. Chris made love to her slowly and with precision and he was sure she liked what he was doing with his mouth. Her fingers were dug deep into his scalp, so he sure hoped so.
“Make love to me,” Lisa was panting. “I need it so, make love to me for as long as you can stand it,” she told him.
“You know, you can talk dirty if you want,” Chris told her. “I don’t mind if you want to let loose a little.”
“I’m not like that,” Lisa groaned. “Come on Chris, put yourself inside of me. I’ll wrap my legs around your back so that you can really go in deep.”
It was at that moment that Chris told himself that his girlfriend must have had more sexual experience than he had. Okay, he was a modern-thinking, liberal guy. If she’d had sex a few times before they hooked, that was perfectly fine. She was committed to him, he was sure of that. His suspicions were confirmed when he entered her pussy and found no impediments. For someone who didn’t like to talk dirty in bed, she sure could move. Boy, could she move!
Chris didn’t get eryaman escort out of bed much for that day. When Lisa finally did go home, he finally understood the term “fucked out”. Lisa had quite literally worn him to a frazzle. It took him a while to realize that they hadn’t had much conversation that night. Most of it had been spent fucking like rabbits.
It took him a number of months filled with great sex (he didn’t mind the great sex) to realize that Lisa was doing this on purpose. She was distracting him from his goal of asking about their future. A future that he discovered would not be including him. Lisa wasn’t brave enough to tell him — a few of their mutual friends showed where their loyalty was.
Lisa was cheating on him. She had been for some time. One of their mutual “friends” was a little more “friendly” than he appeared to be. It would take some years, but Chris would eventually forgive the friend. He knew better than most how manipulative Lisa could be. He wouldn’t be so generous in regards to Lisa. In fact, Lisa was lucky that her now-former boyfriend didn’t leave a boot print on her ass when he kicked her to the curb. Had she said early on that she didn’t want a committed relationship and that she wanted to see others, he might have been fine with it. She hadn’t. She had led him down the garden path and made him believe he was the only man in her life when that simply wasn’t true. Over time, he learned it was as far from the truth as possible. Lisa had cheated on every boyfriend she’d ever had.
The disheartened young man drew himself into his book store and the company of friends. Never a great success with the ladies, for Chris, that didn’t change. He was too insular and only gregarious with people he trusted or in the comfort nook of his store. He had dates here and there, but no one serious. That went on for over a decade. He was in his late 30’s when he met Darla. She was 21 and nice, with a bit of spunk and somewhat quirky. She was a frequent customer at his book store and eventually, they started going out for coffee. The young university student seemed to have a very sharp mind and was witty. He knew the relationship was a friendship because she made sure he knew it. During the span of 2 ½ years, Darla had two fiancés. She liked men and men liked her right back. She was also very committed to the idea of marriage, which Chris thought was charming. He found himself very drawn to the sometimes-funky Darla and looked forward to their “dates” which had now become the occasional lunch and dinner.
Her graduation from university, although expected, took Chris a bit by surprise. She assured him that she cherished their friendship and that nothing would change. He found that hard to believe. He expected it would end, as she lived a 90 minute drive from him. However, Darla proved to be as good as her word. She visited him at least once a week. She was finding her old home boring, she missed her friends and, she kept telling Chris, she missed him most of all. What Chris realized after a number of her visits was how much he was missing her. The funky little country mouse had turned into a sexy, cuddly, curvy sophisticated young city woman who dressed well and made his heart pound. Without his even knowing it, Chris had fallen in love again. He sighed as he talked it over with some trusted friends. All but one assured him that his future with Darla was non-existent and doomed to failure.
“She loves you, you just aren’t aware of it,” Monica told her friend over Yahoo Messenger. “She drives 90 minutes both ways at least once a week to see you. Why not try this ploy? The next time she drives to visit, offer to let her crash at your place. Tell her she can use the bed and you’ll take the couch. I bet you will find she offers to share the bed with you and I bet she will make her move then.”
Chris scoffed at Monica’s suggestion, but she almost bullied him until he agreed that he would try it. There was simply no way his intense feelings for the young Darla would be returned. He knew that if he offered her the bed, she’d take the couch and it would end there.
Poor Chris, he should have known better than to argue with Monica. She was right, she was always right. It was almost as if she was psychic. Everything happened exactly as she had predicted it would, almost line for line.
“Haven’t you noticed I’ve been wearing sexier outfits when I come to visit?” Darla said as she actually sat on his lap and kissed him. Her fingers ran through his head and at the graying temples at his side. “I was beginning to think I’d have to actually jump you.”
“That would have worked,” he chuckled as she nuzzled his neck. “Seriously, I just thought that you were wearing nicer clothes because you could afford them now.”
“Yes, that was a part of it,” the now-successful commodities broker grinned. He touched her cheek and looked into her dark brown eyes. “But I wanted you to notice the sexy young woman. I always wear heels now because I know you like them. You should see what’s under all these sexy clothes.”
“Is that an offer?” Chris teased.
“With eryaman escort bayan a money-back guarantee,” Darla smiled and led him into his own bedroom. She began to undress and the man who loved her began to realize just how smitten with her he had been. Tiny and petite, Darla’s auburn-haired beauty knocked him off his feet. She hadn’t been kidding, the La Pearla lingerie she had worn was designed to titillate. As they indulged themselves with romantic foreplay, he was in no rush to remove it from her. She looked fantastic and if her past visits had set his heart to thumping, this one felt as if it might give him a coronary. No matter — loving Darla was worth risking the medical condition.
He knew much more about Darla’s past than he had about Lisa’s. She was very open about her sexuality. For instance, he knew that she liked girls a great deal and had been with several. She quite happily embraced her bi-sexuality. He also knew that Darla had lost her virginity at a young age and considered herself a bit of a “slut”. It wasn’t something she was embarrassed about because sex was part of the way she motivated herself. She loved being a sexual person and anything that enhanced her enjoyment of sex was welcome in her life.
“You know that I’m here to blow your mind, right?” Darla said as she aggressively shoved Chris back on to his own bed. “Amongst other things.”
“Your hard cock, for example,” Darla said, impatiently tugging his pants down to his ankles. She later told him that she had been waiting for almost a year to fuck him. To this day, Chris had no idea if he had proved to be worth the wait for her. For someone who was so open about herself, Darla could be uncommunicative in other ways.
Her beautiful face was beaming that night as she sucked cock. Chris was smart enough to let her take full control. His sexual experiences had grown since he had been with Lisa, although not by leaps and bounds. Still, he had mastered enough skills so that he didn’t need to rush or worry about cumming too soon. He could let Darla have her fun, which she certainly seemed to be doing. She was fairly noisy as she sucked on him and he found those sounds arousing.
Chris knew that Darla wasn’t perfect and sometimes, she would talk about her own faults. That bothered him at those times, because he did see her as perfect. It was her little flaws that were endearing, both physically and mentally. As she got on top of him and prepared to make love, Chris ignored all her tiny imperfections and focused on the many perfections. Her body was petite and delectable and she began to move. No matter what was wrong with her, she sure could fuck. She was wild in bed and he was about to find out just how wild she could get.
Darla had always insisted that she liked sex, but here was living, breathing, fucking him senseless evidence of that fact. Her body was slamming against him so hard that Chris almost wondered if she was going to leave bruises. Harder and harder the young beauty fucked him and she also bit and scratched and used foul language. He liked the fact that she had acquiesced to one of his little fantasies and kept her stockings and heels on in bed. The new shoes were really sexy and he was sure that she had purchased them just for him. Darla knew about all of his turn-ons; he had almost given her a road map to seduction during their relationship. For instance, she had let her fingernails grow out and was raking his back and shoulder blades with them. It was one of his favorite things to have a woman do; he had always gotten the chills when someone did that.
Darla took complete control as she fucked him and before he could cum, she stopped. She was wearing a smile and a glassy-eyed expression as she stroked his still-hard cock. “We were both about to come and I want that to happen a whole lot later,” she explained. “I’ve been practicing Tantric Sex and I’m learning that an orgasm is a whole lot better if you stretch it out.”
With the way she had poor Chris dazzled, he would have danced the Watusi right there and then if she had asked him to. He nodded and let her explain her theory. All he knew is that he wanted to keep on having sex and he wanted to have it now.
Sensibly, his new playmate didn’t keep him on the hook for too long. Darla got on all fours and told him he could be a bit rough if he liked, that would turn her on. So he slapped her ass, pumped her hard, squeezed her tits and pulled her longer hair. All of it seemed to spur her on, so he just kept on doing it. Again, the moment he was on the precipice of orgasm, Darla pulled away from him and gave them both another time out.
If he had been with any other woman, Chris likely would have been hopping mad. At the very least, he would have said something. Darla had powers that she could exert over him and he was pretty sure that she knew that. He just took a deep breath, relaxed and tried not to think of the appendage between his legs that felt as if it was on fire. After five or so minutes, Darla got on her back. “Fuck me, make me cum,” she begged escort eryaman him. “I’m sure I’ll go through the roof this time, fuck me and don’t hold back anything!”
Chris didn’t intend to hold back, aside from fucking her for a few solid minutes. Her legs wrapped around him and dug into his back. He plunged into her body and fucked her savagely. This time, he held back a bit because if he had not, he would likely have cum on the spot. If indeed Darla was aiming for some metaphysical goal, he would try and help her achieve it. He was curious to see if it worked for him as well.
The sex between the two lovers was indeed wonderful, yet had he to testify under oath; Chris really couldn’t have said it was noticeably better. If it made her happy, he was willing to go along with her whims for now. She wouldn’t always be the controlling partner and there would be opportunities for him to enjoy things in his own way.
Except that, there weren’t. Darla remained adamant that much of their sex life, now begun, stay under her auspices. It created a rift between them, one of several over time. He didn’t like the way that she acted at times and she had annoying habits that were growing worse over time. His lady love acted like an idiot when she went out with her other friends, she would drink a bit too much and had started to smoke cigarettes. She had the annoying habit of leaving phone calls and messages unreturned until it suited her.
Things between the two of them no longer suited Chris, not by a long shot. If their relationship had a hope in hell of surviving, he knew he would have to deal with it. He couldn’t argue with her over the phone and face time was difficult when the other face wasn’t around often enough. He poured his heart out in a long letter and hoped she would read it and accept his hope of reconciling their differences.
Instead, the woman he thought was the other half of his soul rendered him speechless with a letter so full of anger and bile he would not have thought it capable of her. He nearly shriveled under all the vitriol and knew they would never see each other again. He was thrilled that they had never married nor had children, for the loss of this woman very nearly broke him. He retreated into the confines of his store and his work shored him up. As far as Chris was concerned, dating was something he no longer wished to do. It was for younger men and men who were willing to lose. He was not such a man.
There were some temptations set in his path, yet he resisted them. Chris knew they would all end in disaster. The final temptation was entirely one of his own making.
He frequented a lovely little restaurant with a few charming staff members and became friendly with a server named Alex. Alex was a petite, vivacious brunette who always managed to get a smile out of him, even in his dourest moods. After a time, he learned a great deal about her and what he knew, he liked. He wanted to know more and decided one date for coffee would be okay. It was more than okay; it was a wonderful 3 hours of conversation. Chris wondered how someone not half his age could fascinate him so much. She wasn’t even 25 and yet, she had him spellbound. He found himself asking her out on a date, a real date, to a nice restaurant with table service, linen tablecloths and a wine list. The words left his mouth before he could stop them. Chris knew it was okay, because she would say no.
Only, she didn’t. She said yes and she seemed to be thrilled to say so. She said yes a couple of times and told him she had a few outfits she was dying to wear and that she would pick something to “knock his socks off”. He wondered just what the hell he had gotten himself into. What the hell was a man his age doing going out with someone so young?
He went through the next several days in a virtual fog, lost in the thought of this lovely young woman. He would see her at work and she would smile at him and he found himself thinking of their date. He had to take her somewhere nice and he had such a place, a French restaurant with outrageous prices, spectacular food and superb service.
None of that mattered when she showed up for their date. She wore the dress, sexy and black, with heels that matched. The petite, elfin little beauty had somehow transformed into a miniature seductress. Chris was sure that he was speaking, although what words he used he could not readily have told anyone sometime after. At the end of the evening, she hugged him and he could smell the subtle wisp of her perfume. Hours later, he could still feel Alex’s soft arms around his neck. He almost floated through the next day.
A few days later, he was back at her work. He got a few disapproving scowls from Alex’s boss, as she was quite openly flirtatious. Before he could stop himself, Chris asked her out again. She readily accepted and they had another fabulous date. She wore a dress that was red and looked amazing against her skin and with her jet-black hair. There was nothing to be done about it. By the end of their date, Chris was smitten. He felt like the biggest idiot in the world. How had he let this happen? How had he managed to let himself fall in love with someone young enough to be his daughter? He knew the answer, of course. Whenever Alex looked at him with her beautiful, dark eyes, common sense went flying straight out the window.
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