Much to Learn: Best Laid Plans

With thanks to Paolo of Wholebean and I

Sarah and Mark’s Story began here

Six weeks. She was supposed to have six weeks to prepare herself for this encounter. Although Sarah had initially been disappointed that between Mark’s schedule and hers there was no earlier date available for the two of them to get together, she eventually resigned herself to the wait and had diverted her nervous energy toward grand plans and preparations. It would be fine. It would be difficult, but fine.

Then all that changed. Thanks to an unexpected shift in their her schedule and a quick flurry of emails, the five remaining weeks turned into two days. She was excited, very relieved to be unburdened of the wait, but she wasn’t ready. Well, she was ready. Every time she thought of him she knew she was ready, but she thought she’d be more ready. She had planned to use her time to learn how to present herself as the elegant, sophisticated woman she wanted to be, the woman he said he saw somewhere within her. She had planned to learn to properly walk in heels, or maybe just to properly walk, she thought with a wince as a sprained ankle reminded her that she had a good way to go before mastering that fundamental skill.

Still, she did not regret her decision to propose a closer date; not for the anxiety it caused nor for the minor changes that had to be made to his plans for the evening. He wouldn’t be able to stay the night; hardly an ideal way to end after a first spanking. She consoled herself with the reasoning that that they would need to part afterwards eventually, and whether they spent time unconscious together probably made little difference. Besides, it would give her something to look forward to.

Sarah had at least managed a bit of preparation in the days leading up to the meeting. His requests had been so minimal, and she was relieved to have found a way to comply with them, even if it had been by complete accident the night before. Despite her frantic search through each of the three clothing shops in town for the black dress and stockings he had requested, she had come up empty-handed. For the first time she appreciated just how close to the middle of nowhere she must live.

Her luck had changed with a stop at Tesco, of all places, After she had picked up the oranges and toothpaste she had stopped in for, on a whim she wandered through the clothing aisle. They had a dress. A black dress. A little back dress that not only fit, but flattered. A stroll to the end of the aisle yielded a pair of little black boots and stockings. Sometimes the universe does provide. The only downside was that, having only purchased the dress the night before, it still smelled a bit like Tesco. A lot like Tesco, she admitted to herself as she hoped it would air out a bit over the course of the day.

Still, at least she had found the requested outfit, even down to the shoes and stockings. While they didn’t carry the suspender belt get-up she was looking for, she did manage to purchase a pair of stay-ups (well, three pairs- just in case). As she hobbled down the street, she began to realize why so many women were so against these things. They were sticky. And itchy.

And falling, she realized in a panic.

A quick glance in the window of a darkened shop revealed the lacy tops poking out from under the hem of her skirt. She glanced up and down the crowded street. Maybe no one would notice. Her reflection caught her eye. Not a chance, she realized. With her bright pink umbrella and equally garish green coat, she easily stood out from the sombrely dressed crowd, attracting looks from everyone who passed.

Why did she bring the umbrella anyway? It had seemed like a good idea when she left that morning, but was only making it difficult to navigate the crowded street. She tried to weave around her fellow pedestrians, but not a few times wound up getting the umbrella caught between street signs and awnings, adding awkward stops to her journey as she struggled to free the thing before she was trampled.

With a curse, she ducked down an alley to make the emergency adjustment to her wardrobe before the stockings slipped any further, feeling more like a cheap whore than ever. Not even that, she thought to herself. She didn’t have the confidence she associated with such women; she was just incompetent.

She briefly considered writing the whole thing off as a bad idea. She could change into jeans, blame the accelerated schedule for the non-compliance of her outfit, and suffer the consequences. The consequences couldn’t be that bad; it was consequences that she was seeking in the first place wasn’t she?

No, she owed it to him to try. He was taking a chance on her, and she felt obliged to do her best to return the favour. Hopefully he would appreciate the effort, if not the result. Maybe she would get lucky and he would find her feeble attempts at dress-up rather endearing or cute.

Taking a deep breath, she continued down the street, searching for the shop she had looked up the night before. She had scoured the internet for other options, but this was the one place that may have the garment she was looking for. As she approached the shop, she took a deep breath to steel herself before opening the door.

She had never been in an adult shop before, though a quick look around told her that this would be a very gentle introduction. The front of the store could have almost been a lingerie section in any department store, and her fellow patrons looked as though they would easily blend into the crowd of shoppers on the street- more easily that Sarah could, most likely.

Relaxing a bit, she began her search. A few slow laps of the racks, and she was overwhelmed.

“Can I help you?” she heard from behind her. Sarah flinched. The last thing she needed now was some cheerfully sexy, confident, skinny salesperson judgingly sneering over her as she tried to figure out what she needed. Turning to the sales girl, Sarah blinked in surprise. The girl was about her age, and shared not only her larger figure, but also, if the shy smile she offered was any clue, understood her vague insecurity. Sarah smiled and relaxed for the first time since entering the shop.

“Probably,” Sarah replied and began to explain what she was looking for.

Sure enough, a few minutes later Sarah was back outside with a bright pink bag containing her newly purchased suspender belt and simple, seamed stockings that the salesgirl had promised would actually fit. With a new confidence, she bounced (carefully- so as to to avoid any further issues with the stay-ups) down the street. Her confidence lasted just long enough for her to order and slowly sip a coffee before making her way to the toilet to change.

She had heard other girls talking of the difficulty of keeping stocking seams straight. The difficulties in properly donning the garments were multiplied a thousandfold taking into account the small space and lack of mirror or experience.

Finally, she had to admit that further fussing was more likely to ladder them than to make them look any neater and emerged, only to remember with a groan that the suspenders were supposed to go under, not over, her panties. Another several minutes of futzing with fasteners and she emerged again, a bit more frustrated and flushed. A quick check of her phone told her it was time to head to the pub where she was to meet him. She uttered a soft curse and hurried up the street. She needed to arrive first. If she stood a chance to make a good impression at all, she wanted to tuck the ridiculous umbrella out of sight and, more importantly, to be seated; while falling into his arms might later be a good thing, she doubted it would have the same effect following a stumble in a crowded pub.

With a sigh of relief, she settled herself on the corner bench. She had made it in one piece, but this wasn’t what she had imagined at all. Back before they changed the date, they were supposed to meet at the train station. She would stride submissively and confidently down the platform into his arms, her long black cloak and spindly heels making her look like some glamorous actress in an old movie.

She had hoped to feel sexy and sophisticated when next she saw him. Instead, she felt sloppy and soggy- the giant pink umbrella doing much to enhance the first and surprisingly little to mitigate the second. “Too late to do anything else now,” she thought to herself miserably and pulled out a book to pretend to distract herself as she waited.

And then he was there, and she no longer felt miserable or defeated. At his first welcoming hug, she was simply happy.

“You look beautiful today,” Mark said as he sat down, making her blush and smile at her shoes. To hear those few simple words, it had all been worth it.

When the waitress stopped by, he ordered “A pint of whatever she’s having,” and Sarah smiled as she sipped her bitter. She must have some charm if she’d managed to get an Irishman off Guinness!

They talked, though not as long or as deeply as they had at their first meeting. This time they had not met to talk. Even as her mind was consumed with what would happen later that evening, she did her best to hang onto his words as they chatted- the normal conversation of two friends catching up over dinner after a long week. It was light and cheery, as if to defy the significance of their plans later on.

Nearly as soon as their food was finished, they left the pub to find a taxi back to the hotel, a marked departure from their lingering discussion the last time they had met.

She fell silent during the drive, her mind consumed with anticipation and anxiety. He talked to her nearly the whole way back, sharing memories of the neighbourhoods they passed, keeping her with him, keeping her calm.

They checked in, a brief, business-like discussion that brought her out of her musings if only for a moment before her anxiety cam charging back on the way up to the room.

She had imagined that she would be holding his hand by this point, nervously anticipation the commencement of the next stage of their visit. But this was not the case. Between his bag and her own (he had dismissed her protests that she could carry the thing herself), he had no hands free. She lead the way, as though eager to get started, unlocked the door, and held it for him as he manoeuvred through with their bags. After a brief shuffle of belongings she excused herself into the bathroom.

In the few brief moments she was alone, the enormity of what they about to do set in. She didn’t feel any urge to stop or flee, but rather stood rooted to the spot, lost in her thoughts. She mechanically performed a quick check to make sure everything was still in place, as best she could, and emerged to face him.

When she came back into the main room, she found him flipping through channels on the television. Was he delaying? That hardly seemed like him. . . . Oh. Right. This was going to make noise. Settling on a channel, he put down the remote and sat on the bed, indicating that she should sit on the chair facing him. Facing him, it occurred to her that this was new. They had always sat beside each other in the pub, and this felt decidedly different.

“Are you afraid?” he asked without preliminaries.

“No,” she replied honestly. Anxious, yes, but not afraid.

“Are you ready?”

“Yes.” It may have been a half-lie, but no more a lie than the opposite answer.

Sensing her indecision, he leaned in and kissed her, long and gently. She tried to return the gesture, as she had before. She knew he was doing this to please her, to relax her, but he didn’t know that it often had the opposite effect, and certainly did now. How could he have knownn? She’d never told him. She hoped that feeling would change in time, but as much as she tried to enjoy it on this occasion, her mind was caught up in what was to come.

Maintaining his embrace, he began to whisper in her ear between kisses. “In a moment, I will take you over my knee. We will start slow, just as we discussed. If it is getting too much, say ‘yellow’ and I will ease up. ‘Red’ and I will stop. This is an introduction, not discipline. But you will tell me when you need discipline, won’t you?” He grabbed her chin to tilt her head up. The look in his eyes was startlingly intense.

“Yes, Sir,” she replied in a whisper.

“Good girl,” he continued. “Later, I have an implement for you. A bit of a surprise. Something stingy. We will finish with just a little bit of discipline today. For denying yourself.” Pulling away slightly, he looked her in the eye again, wordlessly seeking confirmation of her consent.

She nodded. It may be a rather contrived reason for a punishment, but that didn’t make it any less deserved. She had waited long enough for this, had delayed numerous times in her search for a spanker, made many excuses. The excuses may even have been valid, may have contributed to the specialness of this moment, but it was still a denial of her true nature.

One more quick kiss, and he pulled her over to him, guiding her over one leg. “Comfortable?” he asked as he stroked her back.

“Yes, Sir,” she guessed, digging her toes into the carpet to keep herself in place. It was new. Not uncomfortable, but not a position with which she had any familiarity or anything by which to judge.

She felt his hand caress her bottom over her dress for a moment before she was distracted by a muffled thud, as if something had fallen onto the carpet.

Oh. He was starting.

She had expected. . .something else. Something more. Scolding perhaps? Some kind of lead-up. She had thought the first slap would be somehow significant, but as it was it hardly registered before a repeat of the sound told her he had moved onto the next.

It was an odd sensation, muted by the fabric of her dress. The space between caresses, taps, and spanks blurred as he mixed the three irregularly. There was no precise pattern, but a general trend of increasing strength. After several hard swats he would rub her for a moment before beginning again.

After every few repetitions of this pattern, he would turn to her, rub her back and ask if she was all right. Each time she nodded quickly, not wanting him to stop, and he resumed his work.

The television was saying something about concrete. How many years ago it was considered perfectly acceptable, beautiful even. How fitting, she thought as he spanked on, the two of them caught up in this ancient practice that had decidedly fallen from favour. She stifled a laugh by biting her finger. She may be new to this, but knew that giggling while over the knee was not the smartest idea. Chiding herself, she tried to focus on the spanking. That was why she was here, so why did her attention continue to wander? She wanted to experience this moment.

Unfortunately the strongest sensation of this moment was that of her toes slipping backward on the thin carpeting. She tried to regain her footing, but wasn’t able to hold on for more than a few moments before having to shuffle up again.

Her attention was directed back to her behind as she felt him slowly, tenderly lift her shirt. She held her breath, waiting for the inevitable remark or laugh at whatever she had done wrong with the stockings, but it never came. Had she actually managed to pull it off?

After a few uninterrupted caresses, he began the same pattern over again. The sensation was sharper this time, but still somewhat muted. She realized with a fright that her bottom was becoming somewhat numb. What did that mean? Was she capable of truly feeling a spanking? The sharper swats did register as somewhat painful, and she tried to offer herself into them in a mute attempt to encourage him.

After an eternity that her more logical side told her was probably only a few minutes, she felt his fingers tracing the elastic of her panties before dragging them gently down. As he lowered them, she awkwardly tried to lift herself off of his lap to assist before flopping back down, off-balance. He didn’t seem to mind, though, and resumed his caresses. This time, however, she was distracted from the pleasant touch by another thought: with her awareness on her bottom she now realized that her suspender belt was slipping- definitely slipping- far lower than it should have been. She clearly had done something terribly wrong, purchased the wrong size, worn it incorrectly, some other silly error to which she had been blissfully ignorant until this point. More embarrassed by this than her nakedness, she buried her face in the duvet and prayed that he wouldn’t judge her too harshly for this mistake.

She never knew if he did or not, as he silently began spanking in the same manner as before. She was astonished at the physicality of the stronger spanks, not so much pain or even the impact on her bottom but the resulting shock that propagated through her body. They drove her forward, lifting her toes off the floor and grinding her torso into the mattress. They didn’t hurt as much as she thought they might; she hurt herself more in her daily clumsiness than the whole of the spanking- but the whole-body effect when he gave her a particularly harsh spank always brought her focus back from wherever it had wandered (often to the television, which was now distractingly debating the merits of various paint colours in sitting rooms).

He spanked on, sometimes making a slow circle of her bottom, other times focused on on one spot for more spanks than she could count. Whenever he did this, it first felt mildly warm, a bit stingy. Then she would realize that it had gone from pleasant to quite uncomfortable a while back without her noticing, making her squirm until he moved on.

And then he stopped. His hand slid up her back to rub her shoulders, as he had done periodically, except this time his hand lingered longer. “You’re doing well,” he whispered when she looked up at him. “Can you stand?”

She complied, and he helped her shuffle over to the desk.

“Kneel on the chair, facing the mirror,” he instructed as he pulled the chair out for her.

She knelt as requested, resting her elbows on the pillow he had placed on the desk for her. She glanced up to the mirror to see him pacing behind her, flexing a length of leather between his hands. She smiled when she recognized it. He had sent her a picture of the tawse a week ago, so proud of his new toy. She hadn’t expected to become acquainted with it so soon, but was pleased that he had brought it.

“This is a tawse,” he said as he continued to flex it.

She nodded. She knew the name of the implement, but that was all. He had managed to select an implement for which she had absolutely no associations, no fantasies, no fears. No longer, she thought as she lowered her head and waited for him to begin. After tonight, it would always have special meaning for her, one way or another.

She felt him start to tap her bottom. “It will be just six today,” he softly declared. The taps grew harder, though not consistently; there were plenty of gentle taps mixed in as well. After each harder swat she would wonder, ‘Was that one? Did that one count?’ until-

“Ooof!” Ok, that was one. The pain burned through her, and even as she gasped in protest she knew that she loved it.

A few taps later, he stopped to stroke her hair. “You are doing well,” he murmured, and she nodded into the pillow. “Would you like to look up? Watch yourself in the mirror, but only if you want,” he suggested as he took his position behind her again.

She glanced at her reflection. It was decidedly awkward. The girl in the mirror gave her a ‘What are you looking at?’ glare and she directed her gaze elsewhere. At Him.

His face was fixed in an expression of concentration as he tapped her bottom to line up the next stroke, a bit more tension as he drew the tawse back to deliver the next hard swat. But his expression held more than simple focus. He caught her eye briefly and his expression changed to one of stern admonition. Put firmly in her place, she lowered her gaze again to the desk as he completed her discipline.

The tawse stung, but it didn’t sear so much as sing, sending almost musical notes of pain throughout her body. She had heard that girls tended to have preferences for certain implements over others, and despite her lack of experience she knew she loved this one. It felt solid, real, and each blow seemed to penetrate her shell in a way the hand-spanking hadn’t. She dreaded each swat at the same time she welcomed it. All too soon, he was patting her back, and she slowly realized that he must be telling her it was over. So soon? That was six? How had she lost count on such a small number, and on her first ever spanking?

He pulled her into a hug, then told her to lay on the bed. Unsure of what he intended to do, she lay down carefully, and was both surprised and relieved to feel his weight join hers on the narrow mattress. As he laid next to her, she noticed the sheen of sweat on his forehead. Reaching up to caress his face, she was again taken aback.

‘For me,’ she thought, ‘he did this for me!’ Overcome with gratitude, she hugged into him tighter as he held her.

To be continued