Riding Lessons

A couple weeks ago, Jennifer had made a mistake.

To be fair, it was an excusable mistake. She'd always been intrigued by the idea of the wooden horse, after all. So when she was on a perfectly innocent walk through the woods with her beloved Mistress of a girlfriend, it was only natural that her eyes were drawn to the strange beam just off the path. Especially since it looked so weirdly out of place and at the same time so weirdly perfect for this very purpose.

On closer inspection it turned out to be even weirder when it came to the question of its actual purpose, but also even more suited to tickle Jennifer's fancy. The beam was pretty massive with a roughly square cross section, but with the edges rounded enough that there was no danger of cutting yourself on them. It was also screwed in place rotated at forty-five degrees, so its top formed a balanced peak. Likely it was just the initial step of some future construction, like a bench or something. Not that Jennifer knew of any bench design that required a base like this. Whatever the thing might be, though, it evoked the memories of countless pictures and video snippets featuring hot women riding a very similar contraption while their faces were twisted in an even hotter expression of pain.

"What's so fascinating about this piece of wood?" Mistress had followed to see what was up and was visibly confused about her sub looking at this random beam like she'd just found a nest of Easter eggs or something.

"Well, I was just thinking..." Jennifer could have explained her association, but why tell when you could show instead? Especially since she wanted to know what it would actually feel like. Her cocky mind had always figured that the models were at least partly faking it. Because, sure, it had to be uncomfortable, but it couldn't be that bad, right? Especially not compared to things like a caning so hard that it left your ass bruised and tender for several days. Which Jennifer happily let her Mistress do to her on a regular basis.

She knelt down with the beam between her legs. It was too low to the ground for the real experience, but high enough that Jennifer only had to lower her hips a bit to sit down. She pulled her skirt aside so the only thing between her crotch and the edge were her thin panties. And the not so thin panty liners protecting said panties against the last drops of her current cycle, but whatever.

It was uncomfortable alright. Jennifer shifted a bit to find the best position, but there was no escaping the fact that even such a rounded edge was pretty thin, meaning a lot of weight pressing down on really not a lot of area. And quite a sensitive area at that. It wasn't pain so much as a dull ache that felt startlingly deep, as if the edge had pushed into her a lot further than logic and anatomy dictated. Quite an interesting sensation, and Jennifer could totally see it growing unbearable over time, but for now she found her suspicions confirmed. It really wasn't that bad. Even when she spread her legs a bit to increase the weight on the edge, the ache grew spicier, but not terrible.

"Careful there, or you might give me ideas," her Mistress teased. "The kind of ideas that end with you biting off more than you can chew."

"Hardly," Jennifer said, her masochistic pride immediately rising to the challenge. "You should totally build us the real thing, though. We'd get tons of mileage out of it. Like, I could sit on this all day."

Her Mistress laughed. This beautiful laugh of her that was as cute and genuine as it was a hint at the best kind of trouble.

"You do know that now I'm contractually obliged to make you eat those words, right?"

"Sure." Jennifer made a show of grinding the edge. She held back just enough that her panties wouldn't come to any harm, but that still battered her crotch quite a bit. Actively grinding her pussy against the edge definitely went into the realm of actually painful, but it really wasn't like she had a problem with pain. And on the proper thing she'd only be sitting still anyway. "Make me eat all you want, because this is nothing."

So, yeah, it had definitely been a mistake to challenge her Mistress this blatantly, but to Jennifer being a sub was all about making this kind of mistake. She wasn't surprised when a couple weeks later her Mistress called her into the playroom (a fancy word for their unfinished basement that was mostly used as a storage for tools) where she found herself face to face with an actual wooden horse.

Well, the DIY version of an actual wooden horse, at least. Not the fancy porn version that was one big, smooth triangle. Mistress had built a simple, surprisingly high wooden base, with a beam mounted on top that looked a lot like the one they'd found in the woods.

"A beauty isn't it?" Mistress said. "Don't be shy. Check it out as much as you want. Before long, the two of you are gonna get real intimate."

Calling it a beauty might have been a bit of a stretch. Mistress was good when it came to using her hands (in pretty much every way possible), but her crafts tended to be on the utilitarian side. The base was definitely sturdy, but it was also just a collection of whatever wooden pieces she had found, all nailed together. Some of them even had some frayed edges still, threatening splinters if you weren't careful.

Only the parts you weren't expected to touch when riding the thing, though. The base sported a perfectly filed board on either side where the legs would go, and Jennifer was a little disappointed that the edge at the top was even more rounded than the one in the woods had been. Also more rounded than the other edges of the beam, she found upon closer inspection. Despite her threats, Mistress had put in a lot of diligent work just to literally take the edge off the contraption.

"Are you going soft on me?" Jennifer asked, pointedly running her finger over the blunted ridge.

Mistress just laughed. "Just you wait. You'll be singing to a very different tune before long. But if you're afraid I'm going too easy on you..." She grabbed one of the many coils of rope stashed in the room. "Get naked. I know just the thing to make sure your ride won't be too boring."

Once Jennifer had taken off her clothes and bound back her hair, Mistress made her fold her arms behind her back before binding them in place with a simple but effective chest harness. Jennifer saw the vision, especially when Mistress also prepared some ropes around her ankles. With all her limbs out of the way, it would be hard, if not outright impossible, to support herself, making sure she couldn't take any weight off her crotch.

Less clear was how she was supposed to mount the thing in the first place. The top of the beam was higher than Jennifer's navel. Its height ensured that she wouldn't be able to reach the floor with her toes, but it also required some acrobatics to get up. Or at least so she thought, but once again Mistress proved to be the more practically minded of the two of them. She simply slid two chunks of wood over to act as steps. A few moments later, and with only a little help for balance required, Jennifer once again found herself with a beam between her legs, only that this time she was standing over it instead of kneeling.

"Ready?" Mistress asked.

When Jennifer confirmed that she was more than ready, Mistress made her slowly lower her hips. Right before contact she pried Jennifer's lower lips apart, so the edge would rest right against her unprotected slit.

Jennifer gasped as she sat down. The edge might have been blunted to a smooth curve, but it still offered precious little area to rest her weight on, and it still felt plenty uncomfortable pressing into her crotch. If she really sat there for an extended amount of time, there was a good chance she'd walk away with some serious bruises.

Well, not like Jennifer was a stranger to bruises.

"Second thoughts?"

"As if." Jennifer smirked. "This is nothing."

"I was hoping you'd say that." Mistress gave her a playful pat on the butt and laughed at the new gasp caused by the impact making Jennifer's crotch grind against the edge. "Let's see if it's still nothing once I've got you properly seated. Give me your foot."

Jennifer had thought she already was properly seated. When Mistress lifted her foot, though, and tied it back, she realized how much weight she'd still had on it. Which was still nothing compared to when Mistress tied the other one back as well and kicked the chunks out from under her. Jennifer had to clench her teeth to suppress a groan when her pussy was made to carry her actual full weight, without any subconscious cheating.

It hurt, alright. Not the sharp pain of a cane stroke, or even the blunt pain of the paddle. It was just pressure, crazy intense and unsettlingly deep, feeling like she was agonizingly slowly ripped apart right along her pussy. Every instinct in her body screamed for her to get off that edge.

Of course she couldn't. With her legs bound like this, even clenching her thighs with all her might barely lifted her up, while getting exhausting within seconds. She'd remain seated, whether she liked it or not.

"Still think you can sit there all day?"

Jennifer took a deep breath. It hurt, but it was nothing she couldn't handle. She was pretty sure she'd made it through worse, and she was far to curious how this would go to chicken out at the last moment.

"All day would be crazy, of course, but I could easily do an hour."

Okay, that was a lie. There would be nothing easy about sitting on this thing for an hour. It wasn't even a minute yet and she already felt the ache build up.

"As much as I'd love to make you eat those words, I don't think a full hour is safe. Especially not for the first time. Let's aim for half an hour and see if we even make it that far. But since you're this worried about getting bored..."

Jennifer cursed her big mouth when Mistress brandished the clover clamps. Those things were evil. Merciless metal jaws that made you feel like you'd piss yourself from how hard they crushed your nipples. And as if that wasn't enough, their grip somehow only got even stronger when you pulled on them. Even without the wooden horse part, wearing these thing for half an hour was already plenty punishing by itself.

Of course Jennifer didn't complain. That would have gone against her pride as a masochist sub. Still, she had to bite her tongue pretty hard when her nipples got reintroduced to the hated clamps, and she had to blink several times to stop herself from tearing up.

"And now for the final touch..."

Mistress took some twine and connected the clamps to small iron rings at the front of the beam. She went for only a little bit of tension, but with clover clamps, even a little bit of tension hurt plenty. The moment Mistress had finished the knot, Jennifer leaned forward to stop the clamps from pulling on her poor nipples.

Only to scream as her pussy flared up in pain.

Having the wood press into her slit had been bad enough already. But now that she'd leaned forwards, her weight had shifted right onto her clitoris. Her most sensitive spot, crushed between the entire weight of her body and a thin wooden edge. Jennifer immediately threw herself back, only to scream once more as that made the twine pull taut, yanking at her nipples with brutal force.

Mistress laughed at her misfortune, but showed mercy and helped Jennifer balance by hugging her, stabilizing her in an upright position where her weight rested evenly on her slit and the clamps only pulled a little.

With still hurt like hell, but it was so much better than what Jennifer would have done instinctively, namely throwing herself back and forth several times in a desperate struggle to escape the pain that was most urgent in each moment.

"I think you understand how things work now." Mistress leaned in closer to Jennifer's ear and continued in the most sultry of whispers "I'm gonna have so much fun watching you struggle. You promised me half an hour of entertainment. Let's see if you can deliver."

It took Jennifer decidedly less than half an hour to realize just how much she'd underestimated the wooden horse.

Yes, the edge was diligently rounded, and yes, the pain from sitting down on it was perfectly bearable. That didn't matter, though, because the way the pain accumulated was everything but bearable.

It wasn't that it ramped up slowly. It did ramp up, but there was nothing slow about it. Only a few minutes had passed, and Jennifer's pussy was already tender as if it was bruised all over. Every second that the unyielding edge pressed into it, the ache clawed itself into the soft flesh and barely let go even when she changed her position to shift her weight somewhere else.

And each of these shifts came with a price. A price her nipples had to pay dearly for.

Clover clamps were evil even at the best of times, but in this configuration they were just diabolic. On a moment to moment basis, the pain in Jennifer's crotch was a lot worse than the burning of her nipples. Every time she moved, though, the tug on those crushed nubs made her want to scream. So far she managed to keep her dignity and only groan a bit, but her eyes were already watering and she knew she'd lose the battle soon. Experienced masochist or not, there was only so much abuse something as sensitive as her nipples could take.

Which meant that sooner or later she just had to lean forward to give them a rest. At the expense of shifting all the pressure onto an even more sensitive spot.

After the initial shock, she found that just like with the wooden horse in general, crushing her clit on it didn't hurt in the fiery way like when Mistress used her crop on it. Instead the pain came as an aching pressure that grew and grew until it consumed her every single thought and she couldn't even breathe anymore, forcing her to rock back. And thus the circle continued.

A circle with a rapidly shrinking radius.

At any given moment Jennifer knew that she should stay in her current position a little longer, so all the other hurting parts could recover and it wouldn't be as bad when she had to use them again, but that knowledge held no candle to the pain she was feeling right now. With every iteration her nipples and her pussy grew more and more tender, able to handle less and less pain before Jennifer felt like she'd literally die if she didn't shift immediately. Several times she wished she could lean all the way back and let her ass crack bear the pressure for once. Bruising her back bone as well would make things even worse in the long run, but the mere possibility of moving the pain somewhere new entirely felt like a heavenly luxury.

Of course the clover clamps made sure that this option remained nothing but a wistful dream.

Truth be told, her safeword was already dancing on her tongue. Masochist or not, this was literal torture. She mentally apologized to all the models she'd doubted. Jennifer couldn't imagine bearing this amount of pain for money, especially knowing that innumerable strangers were going to see her come completely undone.

What gave her the strength to hold on was seeing how much her Mistress enjoyed her suffering. Mistress had barely sat down for a minute before getting back up and hovering around Jennifer, biting her nails with a giddy grin. Something she only did when she was really excited by something. Jennifer had no doubt, once this ordeal was over, Mistress would ride her face to several sloppy orgasms.

How amazing that would be, getting to eat her Mistress out, with no hard edge splitting her pussy in two and no clamps threatening to rip her nipples out. What should have been a beacon to hold on to quickly turned into yet another reminder that she really couldn't take this any longer.

"How long?" Jennifer whispered. She had to keep her voice low, for fear that some really pathetic noises would escape her throat.

Mistress gave her nails a rest and took a quick glance at her phone. She was about to answer, but then she just grinned instead.

"How long do you think?"

Jennifer groaned. This could only end in her embracing herself.

How long had it been? Her pussy and her nipples were sore enough that she could have easily believed she'd been sitting here for hours. Of course that couldn't be true. Mistress had set half an hour as a deadline for safety, and she hadn't checked for phone before this moment, meaning they still had to be quite a bit off that mark.

Still, it couldn't be less than fifteen minutes, right? Her pussy couldn't get this bruised this quickly. And given how badly her nipples hurt, the clamps must have been on for a good while already. They, too, never stayed on for more than half an hour at a time, and usually even at the end Jennifer didn't feel like literally crying every time they tugged just the tiniest bit. Which would have been an apt description of her current state, except that her eyes had been watering for quite a while now already.

"Twenty minutes?" she ventured, already bracing herself for being mocked about it only having been five minutes yet.

Mistress didn't mock her, but she also didn't reveal the answer. Instead she completely ignored Jennifer's guess to ask "It's bad, huh?"

"So bad," Jennifer whispered.

Once more she had to lean forward to give her poor nipples a rest, and once more this led to her crushing her clit. Her clit that had been real tender to start with, and had since then been battered and bruised over countless iterations of her riding the horse.

The pain was too much. It shattered whatever had remained of Jennifer's already tenuous self control. She sobbed, the tears now flowing freely. It hurt her pride to be reduced to such a mess after having been so cocky, but that didn't matter right now. Crying was good. Crying helped. It didn't take the pain away, but it let her get at least some of the tension out of her system.

"Aww, you poor girl." Mistress swooped in and gently swiped the tears away. She sounded genuinely sympathetic, but not concerned. Crying was a sign to check in, but not a safeword in itself. "Do you need out?"

After only the tiniest hesitation Jennifer nodded. She simply couldn't deal with the pain any longer.

Luckily it only took a few seconds for Mistress to get the stepping blocks back in place. Not so luckily, the clamps needed to come off first. It was a good thing they were down in the windowless basement, or Jennifer's screams would have echoed through the entire neighborhood. The blood rushed back into her nipples in two spikes of pure agony that made her forget even about her bruised pussy for a moment. That she couldn't even soothe her nipples with her arms bound behind her back didn't make it any better, either.

When Jennifer finally stopped shaking and tried to stand up, she realized just how battered she really was. If not for Mistress catching her, she would have dropped right back down on the edge. A possibility Jennifer didn't even want to imagine. Her entire hip area felt like one giant bruise. Every movement hurt, and she was so tense and stiff, swinging her leg over the beam to get off simply wasn't an option. In the end she had to awkwardly shuffle backwards a bit until Mistress could lift her up from behind and put her down. Good thing Jennifer had a Mistress fit enough for this to be an option.

"You okay?"

Jennifer wiped the rest of the tears from her face. She was standing like a cowboy after a full week in the saddle. Everything hurt. Now that she was off, though, and nothing dug into the bruises anymore, she could think clearly again. She could even grin at how stupid she had to look right now.

"I'm fine," she said. "Just, when I go down on you afterwards, don't take it personally if I don't want any reciprocation."

"Of course." Mistress returned the grin and went for a nice loving kiss. "And I gotta say, you're real brave. That's a brutal predicament. I honestly didn't expect you to make it even half as long as you did."

Jennifer felt the familiar glow that always came with this kind of praise. She might have just cried and thrown in the towel, but she never felt as strong as when Mistress acknowledged how much pain she took upon herself.

And yet she just had to ask the fateful question "So, how long was it?"

"A bit over ten minutes."