Note 1: This to be a story with sexual elements. If you’re looking for a quick rub-and-go, this may not be the story for you
Note 2: Part 1 is a mostly non-sexual background for James and Angella’s relationship. This section is much longer than the others, but the background is relevant to the story, so Part-1 at your own peril
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EARLY YEARS
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At the age of 15 James came across a box filled with pictures of his dad’s old girlfriends. Even though clothing and hairstyles had changed over the years, James found most of the girls to be attractive, and since James was adept at researching and stalking people online, he decided to look up some of his dad’s old flames.
To his surprise, each girl he researched revealed the same shocking detail…..he was more attracted to who these women had become than who they’d been when they were younger. It was that day that James came to terms with the fact older women were not only sexy, but he was more turned on by them than by the girls his own age.
A psychologist might have said that James’ desire for an older woman was due the fact he’d never had a mother figure in his life. His mother had died around the time of his birth, but James knew almost nothing else about her because his dad refused to talk about her, her death or even tell him what her name had been. Tired of being kept in the dark, one night James demanded answers from his dad, and he finally broke. His dad was yelling at him when he screamed, “I crashed the car while driving her to the hospital. She didn’t make it but you did. Is that what you wanted to know? Are you happy now?”
His dad had walked off after saying that and James wondered if his dad blamed himself for the accident or did he blame his son for “choosing” to be born at that exact time. No matter whom his dad blamed, James decided to never ask about his mom again, as the circumstances of her death appeared to overshadow the memory of her life.
James hated that he’d made his dad relive such a torturous event, but if nothing else, it finally helped him understand why his dad had gone to college but failed to get his degree. James had been born during his dad’s senior year of college, and without anyone there to help him, he had chosen to sacrifice his degree, along with his future, to raise his son.
Giving up his degree in order to raise a child had proven to be a huge sacrifice. Without that piece of paper his dad’s promotions were always blocked. His dad was still able to provide for the two of them, but his dad should have been earning three times what he was right now. James knew that, in many ways, he was to blame for their current financial situation. That mix of knowledge and guilt provided all the motivation necessary for James to work hard for his future.
James wasn’t sure how, but he told himself that one day he’d find a way to make everything up to his father. It was unbearable to think that his dad’s sacrifices had meant nothing.
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COFFEE, TEA OR COUGAR?
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When James started college he encountered his first cougar. This wasn’t some slightly older girl, such as a senior flirting with a freshman; this was a “woman”, over twice his age. Once she gave him a taste of the hunger, passion and experience women like her possessed, James knew it’d be very hard to ever date a girl his age again.
Over the next 4-years James excelled in school and had a string of older women take him under their wing, and into their beds. He never stayed with any woman too long but each one taught him more about how to treat and please a woman. Being the good student he was, he became quite adept at charming mature women out of their panties. In fact, James had become so skilled that when he set his eyes on his man-hating liberal arts professor, he was eventually assigned a special “oral exam” in her office, every Tuesday at 3pm.
As James grew closer to graduation, he transitioned from study halls and libraries to a small coffee shop on the other side of town. This particular shop had decent wifi, comfortable chairs and non-coffee snacks that were barely within his budget.
The real advantage of coming to this coffee shop was the fact it was near the business district. This location attracted an older clientele than the chain coffee shops right off the college campus, and that was more than enough reason for him to make the trek across town and fight the traffic.
James was a creature of habit so he always came to the coffee shop at the same time every afternoon; however, one day he arrived early in the morning so he could work on a project. He’d planned on spending most of the day at the shop doing his assignment, but his plans quickly changed when a woman he’d never seen there came walking in.
James couldn’t take his eyes off of her, and despite his project needing his attention, he couldn’t concentrate with her sitting so close to him. He felt himself begin to sweat and his heart raced as he stole glances of her, and he knew that somehow, he had to meet her, but first he’d have to learn everything he could about this woman.
James barely received a passing grade on his project because he spent the entire rest of the day eavesdropping on her conversations and then investigating her online using every new piece of information he gathered.
James began showing up at the coffee shop early every day after that, just so he could watch her from afar, and his persistence paid off. Even though she didn’t post a lot of things online herself, her friends, colleagues and acquaintances had revealed plenty.
Her name was Angella. She was single, never married, a lawyer at a prestigious law firm, and as fate would have it, she had hooked up with a fair number of younger guys.
Over the next month, James became an expert on all things Angella, and when he was confident he could capture and keep her attention, he made his move.
James waited for Angella to set her things down to claim her table before going up to get her coffee. While she stood in line James walked by and discretely swiped both of her pens. Even though that act seemed trivial, he was betting it’d be enough. You see, Angella had a thing about taking notes while on her work calls, and those notes were always handwritten. He suspected she was one of those people that never fully embraced technology since she didn’t grow up with it like he did, but whatever her reason for her insistence on handwritten notes and maintaining a small online footprint, he would use those things to his advantage.
It didn’t take long before he saw her furiously searching for something to write with during her Wednesday morning conference call, and that’s when James became the gentleman and quietly slipped her one of his pens with a smile and a polite nod.
Once the call was over she walked over to his chair to say thank-you and ask if she could keep his pen a little longer. When she approached him she caught the faint scent of his cologne, which happened to be the same one she purchased for any guy she went out with more than once. Sticking out of the top of his book-bag was a copy of her favorite book and sitting next to him was a project board which had the word “separate” spelled “seperate”.
Angella couldn’t help herself when she saw the commonly misspelled word, so she politely pointed out his mistake. His almost coy and appreciative smile drove her to continue the conversation, just as James had believed it would. With the ice broken, James began to put into practice all the things his mature teachers had instilled in him.
After that first day in the coffee shop, things began to move fairly quickly between them, as was her style. However, James had an advantage she knew nothing of. On the side of a bag she always carried, a woman’s crown and the letters “ANG” were embroidered. On a whim he placed that into a search engine and after a bit of luck he discovered two different blogs and one online journal devoted to the same woman, “Queen Angella.”
Seeing how Angella avoided technology whenever she could, James suspected she knew nothing of the very extensive, and thorough, blogs dedicated to her, and it probably never crossed her mind that someone might share the most intimate details of their relationship on the internet for anyone to read. .
Armed with what he knew, James was able to engage her at every turn. He showed her aspects of his personality he knew she’d like, withheld blatant sexual innuendo and remained vague when discussing most other details about himself. Most importantly, he tried to remain a mystery that she needed to solve.
It took less than a week before she brought up the topic of marriage. Once again, James had the advantage because he’d known this would come up. Without missing a beat, James completely shut down any idea of wanting to get married, and he never mentioned wanting kids. As he finished giving his answer, he watched as she tried to hide a smile of approval.
His answers had made Angella ecstatic, for she’d broken things off with every guy who had even brought up the topic of marriage or children. It didn’t matter if a guy mentioned a niece’s birthday party, her experience had taught her that even a mild reference to kids could eventually morph into an offer to “settle down” or start a family. She had a schedule and plan for her life, and being shackled down with a husband and kids wasn’t a part of that plan. She’d worked and sacrificed too much for her career to derail it now. She only needed a man in her life for one thing, and she’d found that there was no shortage of men willing to meet that particular need. For Angella, no matter how well a relationship was going, any hint of wanting to see her domesticated was an immediate relationship death sentence.
Having finally passed all of her tests she asked him out. James accepted, but refused to act too excited. He knew that the harder she had to work to get him into the bedroom, the more she’d want him and quicker the dominatrix side of her take-charge personality would come out. Oh, he had read, in quite some detail, about her sexual fetishes from one of the active bloggers and ex boy-toy of hers. James had gone so far as to contact one one of the bloggers directly, under the guise of wanting to learn how to be more submissive. Through their extensive chats James had learned everything he needed to know about her darker kinks, the sex store she shopped at and was even treated to an insider’s opinion as to what drives a woman like Queen Angella.
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SLOW AND STEADY GOES THE CONTRACT
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James’ first date with Angella was a success and if it had been any other woman, he would have slept with her that night. James had seen the signs and he knew he could have fucked her after a single date, but he wasn’t ready to. This wasn’t just any woman, this was Angella, and he was waiting for just the right time to take their relationship to the next level Yes, he had fucked quite a few older women in the last 4-years, but when it came to Angella, he wanted their first time to mean something. Most importantly, he wanted it to be an experience that neither of them could ever forget.
Over the next six weeks James went out with Angella quite a few times. They had lunch dates, dinner dates, romantic dates, movies dates and even a weekend away. James knew she wanted him, but he also knew that she understood the law when it comes to consent, intention and rape. Angella would never have sex, or engage in any sexual activity, until the guy made the first move
The first time he was with her she’d hint at her darker nature, but she’d only delve deeper into her true desires the second time they slept together However, before they’d have sex the second time she’d present him with an extensive contract nobody ever read. He’d be told the contract was just a formality to show that their relationship was mutual and to prove he wasn’t after her money or possessions. She’d have given him no reason to doubt her and no guy with a hard-on would choose to read a lengthy legal document when he could just sign it and cum.
The contract was, of course, neither routine nor standard by any measure. By making him initiate sex and then sign an iron-clad contract, she would have made it nearly impossible for him to win a case against her in court, no matter what happened in the months ahead. To this date, nobody had ever threatened her with legal action, but she liked knowing that short of killing someone, she was protected no matter what she forced upon him.
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DINNER CONFESSION
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After officially dating her for just over two months, the day arrived when James knew the time was right. He hoped that despite the lack of advanced notice, Angella would jump at the mere hint of him being ready for more. As with everything else, he had read her correctly. When he texted to ask her if they could go back to her place after dinner so they could hang out a bit more….”privately”, she responded by saying, “I have a better idea, let’s skip the restaurant. Come over once you’re finished with class, I’ve got something you can eat”
James played dumb and insisted they go out, because he wanted to celebrate the end of the semester. Reluctantly she agreed, and she was further annoyed when he didn’t take her up on the offer to “step inside for a celebratory appetizer”.
Angella was starting to believe she needed to end things and find some new stud, but when he casually let his hand brush across her ass as she got in his car, her heart raced. There was something about James that had captivated her from their first meeting, and now that he seemed ready, she prayed the wait had been worth it.
At the restaurant he sat next to her, touching her leg and teasing his fingers ever higher until they barely slipped under her skirt. When Angella later excused herself, she came back from the bathroom with more of her blouse unbuttoned. Changing seats, she chose to sit across from him so she could fuel his imagination as to what else she had to offer.
In the following minutes the couple engaged in a coded discussion of their sexual desires, but it was one you’d only pick up on if you listened carefully. As they carried on their seemingly innocent conversation, she looked into his eyes and came to understand that his innocence was merely an act….and she loved the game..
By the time dinner was over, the thought of what she wanted from him had Angella ready to throw her young companion on the table and lower herself onto his body, despite the room full of onlookers. She’d never had to work so hard, or so long, just to get a guy in bed. More than once she wondered if his hard-to-get act was why she felt so horny or why she wanted him so badly right now. The fact was, she’d been horny all day and the only thing that had stopped her from masturbating earlier was his innuendo heavy text about tonight.
When James picked up the dessert menu at the end of their meal Angella broke her non-interference rule as she reached over to stop him. She had been patient with him, and while he seemed more willing to go further tonight, she was tired of waiting and hoped that a little redirection might do him some good. With a finger at the opening of her blouse she pulled her bra lower as she looked at him. Once she was sure she had his attention she said, “No James, that’s not the dessert I think you want. I have something I really want you to eat, and I think you want it too.” She then let her finger trail down between her breast and into her lap suggestively as she said, “So how about we head back to my place so I can give you what you really want.”
She paused for a moment before emphasizing the importance of making the right choice by adding, “but if you’re not interested, you can get something here and I’ll save what I have for someone else. All you have to do is tell me what you want. Do you want a kiddie dessert from that menu, or something a bit more mature at my place?” She slid her hand under her skit and pressed two fingers into her crotch as she continued “I promise you, what I have for you is very warm and so moist I’d actually call it…..wet”
When he didn’t immediately reply her excitement grew. He’d kept her waiting and even now that she was virtually throwing herself at him, he was holding back. It’d been a long time since she’d had a challenge, and from her experience, the more a guy fought to keep control, the more compliant he was once she broke him. Based on the way he was acting, James was setting himself up to be her ultimate submissive pet.
As Angella’s panties dampened at the thought of all the ways she could break him, she gave him a stern and suggestive look as she added, “Trust me, you want what I have, but I need to hear you say you want it or we can’t go further.” She slipped her foot between his legs and into his crotch as she continued, “Once you’ve experienced what I have, you won’t be able to get enough, which is why I will be feeding it to you all night long. I promise, you will become addicted, I already know that. I can see it in your eyes. I already know that after tonight you will agree to anything I ask just to get more.”
A smile touched her lips as she said, “I know that sounds like an exaggeration, but I promise you, it’s not. It’s “that” good.” She then slowed her speech to emphasize the words, “I’m…that good.”
After a brief pause she resumed her thought by asking, “Are you ready for that James? Are you prepared to do exactly what I say in order to get your first taste? Be a good boy and tell me what you want. I need to hear you say it”
James had planned on dragging this out longer, of teasing her through dinner, on the way home and for another hour after getting to her place, but there was something about her that made him want to please her. He genuinely wanted her approval, so before he realized he was speaking he found himself saying, “Yes, I want it.”
Angella smiled as she leaned on the table to get closer to him. Her voice went softer, but it kept the same intensity as she said, “And what is ‘it’ James? Be specific”
James smiled at her and he tried to convey his own growing desire as he said, “You know……..it”
Pain suddenly shot through James as Angella’s foot dug into his cock and forcibly pinned his balls to his leg. Her voice took on a new level of seriousness as she said, “That wasn’t specific, was it?”
James shook his head ‘no’, too afraid to speak, out of fear that the pain radiating through him might be heard in his voice.
Angella relaxed her foot and, as if by magic, she began rubbing and coaxing his cock with her foot once more as she said, “Be a good boy and be specific this time.”
She looked him in the eyes in hopes he’d grasp her seriousness as she said, “Every choice you make leads to reward or punishment. You can be a good boy or bad boy, that decision is yours. Either way I will get what I want from you. Regardless of the path you choose, you will become addicted to pleasing me and the pleasure I let you feel.” Angella leaned in a little further and with a mix of seduction and intimidation she added, “Your decisions dictate the ratio of reward to punishment you experience. If I were you, I’d choose your next words very carefully.”
Angella sat back in her chair and her foot retreated from his lap as the distance between them increased. She stared at James and she could see a hint of conflict in his eyes as he tried to process what had just happened. She had seen that look before. It was the look of someone who had always thought they were in control and couldn’t be pushed around, suddenly realizing they weren’t the alpha in the relationship. It was a look she enjoyed, and one in which she savored. This didn’t mean she’d won the war, but that look in his eyes told her she’d won this battle.
James momentarily forgot about his plan and all the research he’d done on her. Once more he didn’t think before he began saying, “I want to fuck you. I don’t want to wait any longer. Ever since the day we met I’ve thought about what I pray happens tonight. I want to fuck you more than I’ve wanted anything else in my life, and there’s nothing I wouldn’t do to make it happen. I don’t want to wait for tomorrow or next week…I want you tonight. I want us both to remember tonight for the rest of our lives.”
James thought about stopping there, but something drove him on as he confessed his desires. “I’ve purposely been making you wait because I was desperate for you to want tonight as badly as I do. I hoped you’d be so frustrated and anxious that your own expectation would burn every detail of tonight into your memory so that for years to come you’d still remember every single second of our time together.” James barely stopped to breath as he continued, “I know that what we have won’t last, it’s not your style, but I accept that, and if anything, that intensifies my desire for you to remember how badly you wanted me to fuck you. I want it to be crystal clear in your mind that when we fuck tonight it isn’t some drunken accident or heat of the moment madness, instead, I chose to take my time and get to know you before climbing into your bed”
James looked into her eyes with an intensity she hadn’t seen in him before as he added, “I want you to remember that for two months either of us could have walked away from this relationship, but we didn’t. I also want you to know that I didn’t text you today on whim. In fact, roughtly two-weeks ago I circled today’s date on my calendar and then wrote ‘Fuck Angella'”
Angella stared back at him, listening to the most honest, and confusing, confession of need she’d ever heard from a guy. Before she could say anything he continued, “I can see how badly you want me in your eyes, but I promise you that your desire for us to leave here and go back to your place doesn’t exceed my own.” Reaching out James took her hands in his as he finished by saying, “I want you to understand that I’m prepared to let you do anything you want as long as you take me back to your place and fuck me tonight. And I mean it….anything.”
James suddenly realized that he was no longer whispering and people in the restaurant were now staring at him. James instinctively knew that, prior to a few minutes ago, everyone would have believed he was out to eat with a relative, neighbor, co-worker or family friend, but James neither cared that now people knew that wasn’t true nor that they had heard how badly he wanted her. He had meant every word he’d said, and if a few awkward stares was the price to pay so he could fuck her, then he could endure the judgemental gaze. He looked into her eyes as he asked, “Was that specific enough?”
Angella raised her hand to get their waitresses to bring the check. She smiled at her young friend and said, “Good boy. There may be hope for you yet”