by Maggie Ryan
His brow furrowed as he checked his watch. While it had taken Jane a while to ascertain the access code and password, it seemed to be taking quite a bit longer for her to continue. His fingers itched to use the keyboard, but until he was granted permission, he had to wait and patience wasn’t exactly his forte. Not when it pertained to something he’d been waiting to happen for a long time.
“Come on, sweetheart. Don’t be frightened. Click the button and let’s begin our journey.”
A few moments later, he smiled as the woman who had somehow instantly become important to him made her choice. Not wanting to make her wait, he set down his glass and began to type.
Jane, Thank you. I am pleased to see you’ve discovered that I think you are a very special young lady. As you continue on your journey, know that it will be my greatest pleasure to be with you every step of the way.
The following screens will contain a list of questions that only you and I will have access to. I imagine you will find the first no more invasive than ones you’d fill out to apply for a job. The next few will serve to provide some information about your past. The final pages will be far more personal. Know that these are not meant to embarrass or judge you. They are simply a means to allow me to formulate a plan for your exploration of what I sincerely hope will be exactly what you’ve wanted, what you’ve dreamed about and have yet to find. There are no right or wrong answers, and I have no preconceived expectations.
You’ll find that I abhor dishonesty, and, yes, I consider omission to be a lie. As I also believe in complete disclosure, let me be clear. This is not some matchmaking service. I am not interested in dating to see if we are compatible. I already know that we are and believe that you feel the same. Will some of the questions make you uncomfortable… yes. Will some make you blush… I have no doubt they will, and might I say that I find the fact that you blush so easily absolutely adorable.
Will some have you squirming… most likely if you choose to answer dishonestly and I later discover you’ve fibbed. There are consequences for naughtiness. Misbehavior will have you paying a price that will vary depending on the infraction, but will always include making your apology over my knees, or bent over a bed, a chair, the arm of a couch, offering your bare bottom knowing I will indeed make it burn.
Take your time answering as this is a serious step that you are taking. I realize I am asking a great deal… but know that I am committed to guiding you, to disciplining you, and to teaching you all about the pleasures and joy found in submission. I am asking for your honesty and your trust. I promise, I will treasure each and never abuse either.
With anticipation,
Sawyer Masterson
* * *
Holy hell! Jane felt as if she were on an emotional rollercoaster as she read the screen for a second time. The words made her feel both excitement as well as trepidation. It was exactly as Sarah had said… he wasn’t asking her out on a ‘date’. By answering whatever questions were to follow, he was basically skipping several dates where a couple gradually learned more about each other. But was that such a bad thing? She’d dated men before and, even after several weeks, she hadn’t truly known them or felt they knew her true self. She had no idea how this man had been able to exchange only a few words and had managed to discover one of her deepest, darkest secrets. All she knew was that from the moment he’d met her eyes, she’d been lost.
Reading the note again, her eyes lingered on the section about offering her bottom… her bare bottom for his punishment. She’d not truly considered that as something common in a D/s relationship. But then, since she’d never actually been in such a dynamic and only had her fantasies to go by, perhaps it was more standard than she’d thought. Realizing that her buttocks were clenching and her heart racing, she knew she had so much to learn. Maybe it was a good thing to cut to the chase. Still, he would know so much about her and she’d know what? Nothing really… he wasn’t answering any list of questions.
He’d said to take her time, and she was going to take him up on that offer. Sliding off the bed, she left her bedroom in search of Sarah… or more precisely, Sarah’s computer.
“May I borrow your laptop?” Jane asked as she entered the living room.
Sarah looked up from the book she was reading. “Something wrong with yours?”
“No, but I’m afraid that if I change windows, I’ll screw up the questionnaire.”
“Ah, so there really are questions? What is he asking?”
“I don’t know yet. I haven’t gotten that far, but I want to look something up,” Jane said.
“Something or someone?” Sarah asked with a grin.
“All right, I want to google him. Is that an awful thing to do?”
“Hell, no, I think that’s a great idea,” Sarah said, tossing her book aside. “And smart.” She grabbed her laptop and soon a photo of Sawyer Masterson was on the screen.
“Wow, that’s a lot of sites,” Jane said, looking at the lists available that contained some sort of information on Sawyer.
The two continued to click and read snatches about Sawyer’s life. Jane had thought he must be a man of means, but she’d had no idea that he was the owner of a corporation and employed several hundred people.
“He’s very successful, isn’t he?” Jane asked.
“If by successful you mean rich, yeah, I’d say that’s a fact. I’ve heard of Masterson Enterprises, but didn’t connect it with your guy. Hey, there he is with Mr. Arturo.”
Jane saw the photo of her boss and his wife at some sort of fundraiser he’d chaired, but her eyes went to the man beside them. It seemed that he was quite generous as well, presenting Mr. Arturo with a $100,000.00 check to help feed the hungry in the city.
From their searching, they learned that Sawyer was thirty-six, had never married, was a sports fan, and appeared as a regular donor at various charity events.
“Well, girl, I have to say, it seems he’s not only legit, he’s a good guy,” Sarah said and then sighed.
“What?”
“Don’t mind me. I’m just wondering when I’m going to meet someone who thinks I’m a favored one.”
Jane reached over and gave her a hug. “I’m pretty sure Brian sees you that way, and you’ll always be my favorite.”
Sarah hugged her back and then gestured toward the book she’d tossed onto the coffee table. “Not for long. Listen, I’ve seen your Kindle and know we share a love for the same sort of books.”
Jane felt her face flame as the words from her screen popped into her head. “True, but, what if that’s all I can handle? You know, reading about it. I’m not sure I actually want to… well, experience those things.”
Sarah laughed. “Jane, don’t ever play poker. The other players will wipe you out. You can’t lie to save your life. You’ve been looking for a man who will not only love you like you deserve, but keep you on your toes. If this man isn’t saying that he will teach you exactly what he expects, and guide you along the way, then I say don’t bother.” She paused and then added, “Am I right? Do you already have a feeling that Mr. Hunky will be able to meet your needs?”
Releasing the lip she’d been gnawing on, Jane nodded. “I don’t already ‘feel’ it; he practically said those exact words.”
Sarah pulled Jane to her and squeezed. “I thought so, and, damn, girl, I’m really happy for you! I’m really thrilled that you finally might have found the perfect guy.”
Jane knew she was telling the truth. The women had been friends since the first day Jane had begun work at Arturo’s. They had been there for each other in good times and bad and were each other’s strongest supporter. “Thanks, Sarah. Um… would you still feel the same if I tell you that he also said that there will be a price to pay for… misbehavior?”
Sarah canted her head to the side, her brow furrowing a bit. “What sort of price?”
Feeling her buttocks clenching again, Jane took a moment, thinking how to put it and d
ecided the truth was the only way. “He said I’d be expected to present my bottom… my bare bottom and he’d make it burn.”
A grin replaced the questioning look on Sarah’s face. “I’ve always wanted to know what it’s really like to be restrained to one of those spanking benches in those books. I swear, it just makes me quiver.”
“He didn’t mention restraints or spanking benches, but, well, he did mention being over his lap or bent over a bed. It sounded more like… well, how a naughty child is punished instead of some sexy submissive,” Jane said.
“Ah, it sounds like he’s one of those daddy doms.”
“Daddy doms?” Jane felt her tummy flip and suddenly words she’d heard him utter took on a new meaning. Good girl. Adorable. Little one. Naughtiness. Looking up, she saw Sarah smiling. “You really think so? I-I didn’t even consider that.” She paused, silently thinking that wasn’t exactly the truth. Her Kindle was full of books based on a dynamic called ageplay. It had her thinking of all sorts of things, and, to be honest, shuddering quite a bit and not in horror. “Don’t you think that’s… well, a little weird?”
“Honey, it takes all kinds of people to make up this fascinating thing we call life. If having a daddy dom is what makes your little heart go pitter-patter and dampens your panties, then don’t you dare let anyone tell you it’s weird or wrong. You’re a big girl and only you can really know what makes you feel complete.”
“You’re a very good friend,” Jane said, giving her a hug.
“I love you too,” Sarah said, reaching for her book. “Now, don’t you have something better to do?”
“Oh!” Jane said, springing up from the couch and dashing back to her bedroom. Jumping onto her bed, she reached for the glass on her nightstand, took a long drink of Coke, and then set it down. “All right, let’s see what you want to know.”
She smiled when the first screen popped up. It asked about her education and her experiences. She giggled as she wondered what he’d say if she asked him to clarify exactly what experiences he was referring to. Then she considered the fact that this screen was asking about her work history, so simply gave the list of jobs she’d held since high school. Pausing, she questioned how he could be interested in her. He obviously had far more education and experience than she had. Taking advantage of the fact that there was a text box at the bottom of the screen, she entered the fact that she’d been saving up to go to culinary school. It wasn’t as glamorous as being a philanthropist, but it was her dream. Clicking on the continue button brought up a new screen. These questions asked about her family.
Yes, her parents were still living and, no, she didn’t have any siblings. Did she consider herself close to her family? She paused, wondering how to answer. She’d been a ‘surprise,’ her mother thirty-eight when she’d been born, her father in his mid-forties. While she’d never really felt unwanted, she’d always believed she’d been a bit of an imposition. Still, it wouldn’t seem right to say she wasn’t close as she figured if push came to shove, she’d be able to rely on some form of support. Clicking the ‘yes’ box, she continued.
The medical ones were relatively easy as she’d had the chickenpox but not measles, had received the normal vaccines as a child, had never been hospitalized, had no known allergies, and had never broken any bones. She blushed a bit when checking that she’d lost her virginity at seventeen, never had an STD, and, no, while she didn’t take the pill, she did practice birth control by receiving a shot every three months. She clicked box after box then hit continue and waited for the next questions to appear.
It wasn’t until the fourth screen that she squirmed a bit. These were definitely more invasive but, then again, far better than having to actually look him, or anyone really, in the eye and give her answers. Perhaps this was just a way to cut through all the things one hesitates to discuss? Better to answer in the privacy of her own room, looking at a screen, right? How many sexual partners would be considered too many? One… two? When she realized her fingertip was scrolling the little arrow up and down, she giggled. If there were that many numbers to choose from, she was probably safe with the truth. She’d had three. Okay, that wasn’t so hard, was it? No lightning bolt had shot through the ceiling, and no disapproving chorus of ‘Jezebel’ rang out.
Oh, Lord! Seriously? Did he really need to know these things? How did knowing if she found it easy to reach orgasm help him? So he can know how long you’ll be writhing and begging before gazing into your eyes as you come apart in his arms, of course.
She considered fibbing a bit about her sexual encounters, suddenly wondering if she was as inexperienced as these questions were making her feel. Far from virginal, she was beginning to feel a bit inadequate. No, she never came from vaginal penetration alone, and she had no idea if anal penetration would get her off as she’d never been brave enough to try that. The very thought made her both squirm and blush furiously. Yes, clitoral stimulation was usually a surety in making her climax. Did she masturbate and, if so, how often? Did she use toys in pleasuring herself? And, shit… did some women really come from nipple stimulation alone? “Lucky ladies,” she whispered as she moved to the next screen.
Hard limits. Thanks to her choice of reading materials, she at least knew what most of these were. But how was she supposed to know if they were off-limits if she’d never tried some… okay, almost all of them? Could she even consider that pathetic smack of her last boyfriend’s hand against her ass—her denim-covered ass—to be a spanking? It had taken her a lot of courage to ask for Joe to try a little kink, and after only a few strokes, he’d informed her that he felt it ridiculous for a grown woman to want to be spanked. She’d felt humiliated. It had been her first quasi-spanking and their last date. So, she couldn’t honestly tick off that she didn’t want to at least experience a paddle, a hairbrush, and call her a fool, but her sex had always clenched when reading about the sound of a belt swishing through the air before it landed with a solid thwack on a bare butt. How would she know if the ‘line of fire’ often described would have her howling and swearing never again, or if it would have her promising to be a good girl? She clicked and unclicked several boxes, changing her answers as she tried to decide what she should enter.
She screamed and practically fell off the bed when suddenly a box appeared superimposed over the list. Oh, God, how could she possibly have forgotten that he was able to see what she was doing?
Jane? Honey, it appears you are having a bit of difficulty. I wanted to assure you that these answers are not chiseled in stone. If you haven’t any experience with a question, leave it blank. As we try different implements, positions, and scenarios, you will be able to fill in your answer with honesty. Even then, as you grow and become familiar with various options, what might be a hard limit at first, might change. Remember, there is no judgment, no right or wrong answer. I hope that helps?
It did. She saw a box beneath his and typed: Yes, sir. It helps—a lot. Thank you.
You’re welcome, little one. If you have any questions, please do not hesitate to ask. I’m here for as long as you need, okay?
She smiled and quickly typed: Okay.
Leaving most of the boxes blank, she moved on to the next screen. This section had her heart beating faster. It also had her digging deep. No, she’d not been spanked as a child. Punishment consisted of being sent to her room or grounded. Yes, she sometimes felt overwhelmed. Yes, she thought being held accountable helped a person make better decisions.
After clicking that box, she wondered if she was somehow sealing her fate. Would he consider accountability could only be learned after turning her ass into a burning inferno as his note had stated?
Inferno? Okay, fine, that had been her little addition. Surely he hadn’t been completely serious about even the use of the word ‘burn’. It was very likely he was using words that painted a picture, allowing them to make his submissive shudder with anticipation. Still, from these questions, it seemed she could expect no
t to sit comfortably if she disappointed him in some way. With a sigh, she decided to leave the answers she’d given alone. As he’d just said, they weren’t chiseled in stone. The last question had her tummy tingling and her mind in a tug of war with her heart.
Have you ever fantasized about having a daddy? She didn’t have to wonder what sort of daddy. These questions, this entire website, had nothing to do with biological parenting. This was about roleplaying, fantasy, adults choosing to explore and experience all sorts of sexual kink and erotic play together. But no matter what Sarah had said, if Mr. Masterson was truly a daddy dom, could she be the type of submissive he was looking for? Did she even want to be?
Granted, she didn’t own a single piece of sexy-as-sin lingerie, but could she picture herself in some outfit meant to regress her to an age far beneath her chronological one? And God, what if he wanted to treat her as one would an infant? Could she drink from a bottle or wear a diaper? Would he stick a pacifier into her mouth whenever he didn’t wish to listen to her? Would she be able to give up her own thoughts, her voice? Finally, with a sigh, she unclicked the ‘Yes’ box, changing her answer to ‘No,’ then unclicking it as well.
Her finger hovered over the power button on her laptop and yet she didn’t push it. Even though she’d not done it on purpose, she felt she had led him on and now owed him an apology. She began to type in the text box in the lower left corner of her screen.
Daddy…
With a gasp, she pounded the backspace button after realizing what she’d just entered. Taking a deep breath, she began again.
Mr. Masterson—Please don’t think that I am judging you or your beliefs, but I feel I must decline your invitation. I do think that you will make some woman very happy… someone waiting to be your special little girl… I just don’t think it can be me.
Jane
Sending the text, she didn’t wait to see if he would respond, not trusting herself to remain strong and listen to her head and not her heart. This time, she pressed the button to power off her computer and shut the lid. She couldn’t help but feel a sense of loss at knowing her journey was over before it began, but she understood the truth. Fantasy was just that… an illusion.
