The top compartment of the chest contained what seemed like a sexy, leather outfit. It wasn’t big, just a few leather straps, metal buckles and barely any fabric between them, more of a harness than an outfit really.
Jessie held it out in front of her, wondering whether she should feel embarrassed, amused or affronted.
She wasn’t supposed to be rummaging through her friend’s private property of course, there was no reason for her to be upset to discover he owned a thing like this, nor any of the others she’d found in that chest. While she did feel a bit embarrassed for finding this obviously private collection and amused for discovering his secret; she was mostly intrigued, turned on even.
When Jessie thought of her own sexual desires, she had to admit she shared some with her friend, without him knowing. She however did not own any leather outfits, wooden paddles, long-tailed whips, ball-gags or any of the other things she might discover in that chest.
She should just put it all back and forget she’d found it. She could also examine it further, knowing he’d never find out if she just put things back the way she’d found them. It was a bit of a shame, she thought, that he’d be returning home this evening. She’d been coming over to his house to feed his cat for a whole week now and she’d only discovered this today.
Still, there were many hours left before he’d be back. She eyed the outfit she was still holding in her hands, wondering if it would fit her.
Jessie blushed as she took off her clothes, undressing down to her skin in her friend’s bedroom, yet the piece was obviously meant to be worn with nothing underneath.
She felt a naughty surge of excitement to stand there naked, worried for a moment that he might return early. ‘Don’t be a chicken.’ She told herself. She’d helped him order those plane-tickets, she knew there was more than enough time before he got back.
The leather harness fit snugly, very snugly, she had to pull hard on the leather straps; watching in the standing mirror to fit them through the buckle on her lower back.
There was a small padlock in the front, but no keys to be found. Jessie wondered whether it was purely decorative or served an actual purpose. It only secured the narrow leather thong that ran from the leather cup against her crotch up between her buttocks, to the back.
It didn’t seem like it could do much harm that way as she played with it in her hands, daring herself…
With a click, the lock closed.
Several hours later, Matthew arrived home. It had been a long journey, he was tired and ready for bed.
To his surprise, the lights were on when he opened the door. His cat Whiskers greeted him at the door. He wondered if Jessie had forgotten to turn them off when she’d come to feed him.
Jessie however, was waiting for him as he rolled his luggage into his living-room.
“Hi Mat.” She said, for some reason blushing furiously.
“Hey Jessie.” He replied. “You’re here late, forgot to feed Whiskers today?”
“No, I mean, yes that’s why I was here, but then…”
Mat raised an eyebrow in confusion. Something was off about his friend, but he was too tired to see what it was. She was wearing a long coat as if she’d only just arrived or about to leave. Underneath her legs were bare, but it wasn’t really the right kind of weather to go outside without trousers or at least stockings underneath a short skirt.
He realized he was still standing in the doorway, so he pushed his luggage aside and dropped into his couch as Jessie began to explain.
“I couldn’t find Whiskers when I got here today.” She said. “I looked everywhere. You told me he never went outside and I began to panic, what if I’d left a window open, what if he was lost because of me…”
Matthew smiled. “Don’t worry, I just saw him in the hallway.”
Jessie blushed again. “Yeah I know, but I couldn’t find him at first, you have to believe me. I looked everywhere, in the craziest places, places I knew he couldn’t be, but I couldn’t stop myself from looking. The top shelves of the kitchen cabinets he can’t even reach, the small closet behind the toilet he can’t even fit in…”
Matthew laughed. “I know the feeling, I’ve done the same in the past. Even went so far as looking beneath the pillow-seats of the couch.”
Jessie bit her lip. “The chest in your wardrobe…”
Matthew’s laugh stopped. That was not where he’d expected this conversation to end. “I’m guessing you didn’t find him in there.” He said, trying to remain humorous about it.
Jessie smiled shyly. “No, and don’t get me wrong, I don’t think there’s anything wrong with owning such things. In fact, I would’ve just pretended to have never seen if I could…”
Matthew raised his eyebrow again. “But…” He said.
“But there was this outfit.” Jessie said, talking fast to get it out. “I couldn’t help myself, I tried it on and now I can’t get it off.” Her hands brushed her coat as if indicating that was what she was still wearing underneath.
Air whistled through Matthew’s pouted lips as he stared at his friend in surprise. “Why did you put it on?” He asked.
“I told you, I couldn’t resist.” Jessie replied with a blush. “I just wanted to know how it felt, please, can you just give me the key so I can take it off?”
“Wait here.” Matthew replied. He left for just a moment, to fetch the keys where he kept them in his room, separate and safe.
“Why did you lock it?” Matthew asked when he returned.
Jessie had tried to get it off of course, tried for hours. It was easy enough to undo the buckle on her lower back and to loosen the collar that went around her neck. To pull the harness on however, she’d had to pull that collar over her head and with the bottom of her outfit firmly clasped around her crotch, she could not lift it high enough, no matter how far she bended forward.
“I didn’t think it would matter.” She replied. “I thought maybe it was decorative or meant to attach other things.”
Matthew grinned. “Other things? Never mind, are you sure that’s the only reason?”
Jessie blushed. “What else?”
“Well, the outfit, like most things in that chest are meant to make you feel helpless, out of control. If you really wanted to know how it felt, to really feel out of control, you would’ve had to use that lock, otherwise you’d always have the opportunity to just take it off.” Matthew explained.
Jessie licked her lips. “Sure, I guess, that was part of it too. Can I please get the key now?”
“Of course.” Matthew said, holding out his hand to give them to her. “So did you like it?”
Jessie hesitated. “Like what?”
“A little.” She admitted with a blush.
“Does it turn you on now?” Matthew asked. “Knowing that I’m in control and not you. That I’m literally holding the keys to your predicament?”
Jessie bit her lip. Her heart was racing, the leather harness was incredibly tight underneath her coat. She was excited, very excited. “It does.” She admitted again.
“What do you think I could do, while I have this control over you?” Matthew asked.
The keys were within her reach, Matthew still held them out as if offering them to her. Something made her keep talking however. “I don’t know.” She replied.
“It’s not often that a beautiful young woman such as yourself puts on that outfit, you know.” Matthew said. “Don’t you think I deserve to at least see how it fits you before I give you these keys?”
Jessie blushed even deeper. Matthew however still held the keys dangling in front of her. The choice was entirely hers. She could grab them. Instead, she began to unbutton her coat.
Matthew eyed her eagerly, hungry.
Jessie dropped her coat on the floor, she felt naked without it. The leather harness did very little to cover her body and nothing to hide her curves.
At the center of the broad collar around her neck, a narrow strip of leather rand down between her breasts. Attached to it were two leather straps, they widened a little where they covered her bosom, yet with plenty of bare skin visible all around. Narrowing again beside her breasts, the straps crossed first her back and connected to a metal ring at her belly-button. From this ring two more leather straps wrapped her body, secured by the metal buckle on her lower back. If you undid that buckle and unwrapped the leather straps, she’d be naked from her crotch all the way to her neck; or you could just undo the zippers at the center of the wider part that covered her bossom to free her breasts.
The narrow strip of leather that originated at her collar ran all the way to her crotch, passing underneath the broader straps that kept the upper part of the harness in place. It was just wide enough to cover her crotch before it split into two leather thongs that ran up between her buttocks. These split up through a knot in the back and ran back to the front over her hips, they connected to a small metal ring on the leather right above her crotch and were be secured by the padlock.
She couldn’t pull it down with the collar still around her neck and she could not pull that up while the padlock kept the thongs resting snugly between her butt-cheeks.
She blushed slightly, but twice as aroused as before now that Matthew was watching her. From the moment she’d heard the padlock close, she’d known it would end this way, with him seeing her like this.
“You look gorgeous.” Matthew said. “Absolutely perfect and sexy. Please turn around so I can see it completely.”
Jessie bit her lips, but did a slow twirl. She wondered how much more he was going to ask of her. But then again, he was still holding out those keys. She only did what she wanted to do. She blushed when she felt him staring at her bare bottom.
“Did you play with any of the other things you found in the chest?” Matthew asked when she still did not reach for the keys?
Jessie licked her lips. “No.” She replied. She’d almost forgotten those, preoccupied as she was with trying to get this thing off.
“Okay then. Well take the keys, you’ve earned them.” Matthew said, though his tone implied she’d earned more than that.
Jessie finally took them, finding the smallest key on the ring that she thought would fit this lock. She should turn away now, find some privacy to get dressed.
“Is it often that you find a woman willing to play with those other toys?” She asked him instead, mimicking what he’d said before.
“Not really.” Matthew replied. “And even less often one that truly deserves it, going around, fiddling with my private belongings and all.”
Jessie blushed, there was a challenge in his voice and not even a very subtle one. Where the leather outfit left her skin bare, her hair stood up in excited shivers. Her whole body tingled, her crotch and breast glowing beneath their snug confinement. She made her choice.
Jessie handed the keys back to Matthew. “Perhaps you shouldn’t give these to me until I’ve truly earned them.” She said.
Matthew licked his lips, his tiredness forgotten after his long journey home. Even his surprise at finding Jessie waiting for him, wearing the leather outfit he’d kept in a secret chest in his wardrobe had dwindled.
He’d fully expected her to take the keys right away when he’d offered. Yet she kept refusing to accept them, keeping their conversation going instead, even when he knew it embarrassed her to admit what she’d done and why.
His arousal, awakened by the idea of her wearing the outfit, surged when he watched her take off her coat, revealing her near-naked body clad in straps of leather.
And now, she’d given him back those keys. He tucked them away in his pocket, showing he was truly in control now.
“Since you seem to like going through my things.” He said. “You’ll go back upstairs now and choose something from that chest that I can use to teach you a lesson about respecting others’ private property, young lady.”
He’d given the command as a test to see how submissive she’d be and to give himself some time to think while she was out of his sight.
Jessie nodded and turned away, heading towards the stairs that were located between the living-room and his kitchen.
“Oh and Jessie, since you’re wearing that outfit, I want you to call me Sir from now on, until we’re done.” He called after her.
His friend froze and turned around with a blush. “Yes, Sir.” She said, before continuing on her way.
Matthew stared avidly at her bare bottom as she mounted the stairs. The way she moved could only be described in one way: eager. She was yearning to discover what would happen if she submitted to him.
It wasn’t really about teaching her a lesson, about being angry that she’d messed around with his personal belongings. It was two people discovering a shared interest; it was a fantasy that needed to be fulfilled, a desire in him and her that had to be met. They had to keep going, for if they stopped, when they had time to think, the opportunity might be lost.
When Jessie returned, bringing him a riding crop from his chest, she looked hesitant. Matthew wondered whether she’d had too much time to think after all, on her way upstairs.
Her arousal was too great however, it rushed her forward, pushing her own objections aside. That part of herself knew perfectly what it wanted.
“Will this do, Sir?” She asked, handing him the implement.
“It will do fine, Jessie.” He said, wondering why the riding crop was the implement of her choice.
“Have you ever been spanked before?” He asked her. There was no need to tell her that was what he was going to do. She’d known what items his chest contained before he’d send her to fetch one.
“No, Sir.” She confessed.
Matthew smiled. That had been his guess too. The riding crop certainly looked less wicked than the wooden paddles or leather whips in his collection. It would seem the safer choice for someone slightly nervous, no matter how excited she was.
He placed the riding crop on the small coffee-table beside his couch. “I’ll use only my hands to start.” He said. “To see how well you can take it; and if you can, that will be a good warm-up before we use the riding crop, understand?”
“Yes, Sir.” Jessie nodded excitedly.
“Now, you shouldn’t be smiling that much.” Matthew said, smiling himself to indicate he was only half-serious. “I really do intend to teach you a proper lesson, Jessie.”
“Yes, Sir.” Jessie said again, this time blushing and seemingly a bit more nervous.
“Now, get across my knee, young lady.” Matthew ordered as he sat back down on his couch.
Jessie came forward eagerly. She moaned softly as the leather harness dug into her skin when she bent forward.
Matthew placed his right hand on her bottom. The leather thongs did nothing to cover that; the leather outfit would offer no protection during this bare-bottom spanking. In fact, it left more of her body bare than not, something he was well aware of as he felt her weight settle across his lap.
He wondered if he should say something; but everything seemed to have been said. Jessie lay across his lap, ready to receive her punishment. He raised his hand and smacked her bottom gently.
Jessie moaned softly as he landed mild, gentle smacks all across her backside. He didn’t want to spank her too hard, not yet. He wanted to enjoy the feeling of her soft, delicate skin in the palm of his hand.
He tried a few firmer smacks, just to see her soft flesh ripple away from the impact, her buttocks bouncing when he hit them harder still.
Jessie squealed softly, more from surprise than anything else, when he landed that first really firm swat. The sound made Matthew’s heart race. He was no longer interested in caressing her soft skin, he wanted to hear her squeal again, to hear those sounds she was unable to hold back, those that showed that she was no longer in control of her reactions and her body.
Jessie did not squeal again immediately, even though he landed one firm swat after the other. She did moan loudly though as a pink glow began to appear in her backside, her bare bottom slowly warming up to her spanking.
Confident from her reactions, Matthew knew his friend could take more. Her moans were of pleasure more often than of pain; the movement of her body, rocking with the rhythm of her spanking, was not meant to escape the onslaught of his hand, but to invite his hand to punish her bottom again and again.
He spanked her harder again, landing firm, full-handed swats across her bare bottom. He swung his arm to full effect, the sound of each swat echoing in the room. This was what he considered a true spanking. Not the climactic conclusion, not yet, but the part where the spanking didn’t just sting, but began to actually hurt.
Jessie squealed now as often as she moaned, yet still rocking her body in an excited trance. Her bottom colored red, she even kicked her legs, but did not protest or fight against him while she did.
Matthew grunted, fighting his own excitement as he spanked his friend. He’d been ready to stop after those first few harder swats. Not everyone enjoyed pain, not even if they did enjoy a bit of sting and the thought of being dominated.
Combined with her loss of control and the sexy, revealing outfit she wore however, pain seemed to be the fitting third part to Jessie’s excited. Even while she squealed, her moans were deeper and longer.
The spanking continued, hard firm swats that made her squeal and moan, kick her legs and squirm were she lat across his lap. Matthew reveled in the sounds of her discomfort, enjoying the pain he was causing as much as the feeling of power over his helpless friend and her soft, glowing backside.
Even as she kicked her legs in pain, Jessie rubbed her near-naked body against his, yearning for that intimate touch. And this was the reason why Matthew finally stopped the onslaught on her backside. The sight of her bare, red bottom, bouncing beneath the palm of his hand, combined with her leather-clad body across his lap, rubbing against his crotch was nearly too much to bear.
“Get up.” He said, helping his friend stand up.
Her hair was disheveled from tossing her head. The leather harness dug into her skin, emphasizing the nakedness of her body. Her eyes were large, filled with excitement, yet her lips were glowing red, raw where she had bitten them to deal with the sting in her backside.
“I must say, you took your spanking very well, Jessie.” He said.
She blushed. “Thank you, Sir.”
“Unfortunately for you however, that means we’re not done yet. There is still that riding crop you brought me.” He paused for a breath. “Unless I’m wrong and you can’t take any more?”
Jessie bit her lip. Her bottom was on fire. She’d never thought a spanking could hurt this much. She’d never thought anything could hurt this much and she’d still be able to enjoy it. Yet the truth was, if Matthew hadn’t let her up, she’d still be squirming across his lap, taking every bit of what he had to offer without protest.
To be perfectly honest, she’d been slightly disappointed when he stopped. Yet at the same time, she was hesitant to admit she could take more. How much would that riding crop hurt, she wondered?
She didn’t have to, she realized. It had surprised her how much in control she was of what happened. Matthew had offered her a way out at every turn. Yet at the same time she’d felt like she had no control at all. Especially when she’d been across his lap, squealing and moaning. If he picked up that riding crop, it would be the same all over again.
“I can take a bit more, Sir.” She replied. She wasn’t surprised at her answer. She didn’t know how far she was willing to go, but after what she’d done so far, not much would surprise her still. This evening was just one long rollercoaster ride and she did not intend to get off before they reached the end.
“Stand by the couch.” Matthew ordered her. “Place your hands on the seat.”
Jessie did as she was told, bending over sharply, the leather-harness dug into her body, reminding her of how exposed she was.
Matthew placed his hand on her bottom, it felt like fire on her sensitive skin. “Spread your legs.” He said. “Your muscles are too taut; you’re bent over too far, it will hurt less if you can relax them a little.”
Jessie blushed and slowly began spreading her legs, until she found a position where she could still stand comfortably, but also relax the muscles in her backside.
“Better.” Matthew said, as he was now able to squeeze her sore bottom.
Jessie moaned, wondering how exposed the was at this moment. The leather harness covered her crotch, but she wasn’t sure where exactly the leather splut up into a pair of thongs running up between her buttocks. Bent over as she was, it might not be enough to cover her pussy completely. Did she really feel a gust of cool air against her lips when Matthew removed his hand, or was that only her imagination?
The thought strangely did not embarrass her and she nearly forgot about it as Matthew placed the leather tip of the riding crop against her backside. Why would a bit of nudity embarrass her after he’d already seen her in that much sexier, kinky, leather harness?
The riding crop moved downwards however, stroking her inner thigh, teasing her before he’d spank her. When it moved back up, there was no mistaking it, it touched the bare, wet lips of her pussy. Jessie bit her lip, okay perhaps she did still have some shame in being so exposed, but there was nowhere for her to hide.
Suddenly, the leather tip of the riding crop bit her bottom. A deep sting in a small, concentrated spot made her squeal. Dozens more followed, little fires lighting up all across her backside and even her upper thighs, re-igniting he pain she’d felt from before.
It was very different from the full, heavy swats of Matthew’s hand. It didn’t go as deep, nor did it make her bottom bounce. But the sting of each bite remained longer, glowing in concentrated spots on her backside, and more kept coming until her entire bottom felt aflame.
“Are you learning a lesson, young lady?” Matthew suddenly asked her. Some little flames winking out in her backside as he paused the torment of her bottom. There were still dozens left however.
“Yes, Sir.” She said and she realized she meant it. Not a lesson about respecting his property; but learning that a spanking could hurt, that if she wanted one, she’d have to accept the pain that would come with it, the price she had to pay for the pleasure that came with it. A price that was pleasure in itself in some way. She wondered if Matthew knew what she was thinking, ‘a lesson’ he had said, not indicating a particular one. He’d know she was enjoying this too much to feel any remorse for going through his things.
Jessie squealed when a sudden dozen or so swats landed across her backside and more aimed for her upper and inner thighs. Until suddenly Matthew dropped the riding crop on the couch, placing his hand back on her bottom.
He gave her two firm swats, and then said: “You can get up now.”
Jessie moaned, pushing her bottom against his hand. It was glowing hot on her sore backside, and much too close to her exposed, private parts. Yet she didn’t want for it to be over yet.
Matthew landed a few more swats on her stinging backside. “If you don’t get up, I’ll have to assume you want some more.” He said, followed by a few even harder ones that made her squeal.
Jessie bit her lower lip but did not protest.
Matthew’s finger ran alongside the leather thongs between her buttocks. Ending right on top of her pussy, just the narrow strip of leather separating them. “Or perhaps this is what you want?” He asked.
Jessie whimpered. “Yes, Sir.” She managed.
Matthew’s fingers pushed and slipped between the leather tongs, between her lips, thrusted into her wet pussy. Jessie moaned deeply. She’d been right, the leather harness hadn’t protected her modesty in the slightest.
Matthew played with her pussy, thrusting, stroking, finding the most sensitive spot inside of her.
Jessie shuddered, she was shaking on her legs, her bottom was on fire, her pussy filled with at least three of her friend’s fingers, the harness as tight as ever across her body.
She squealed as she came, shuddering and moaning. Matthew’s arm around her waist the only thing that kept her from collapsing on the couch.
“Now you’ve truly earned these.” Matthew said as Jessie finally pushed herself up from the couch and turned around.
She blushed as she accepted the keys, being reminded of how this had all begun. She’d just been curious about the outfit, just wanted to try it on. One thing had led to another, the more she discovered, the more excited she got and the more she’d wanted to do.
Nothing would be the same again between her and Matthew she realized; not after she’d let him spank her, after she’d felt his fingers inside of her.
They’d been friends for a long time, but never more. She’d never really seen him as a potential partner. It didn’t seem like they had that much in common. Yet at least this interest they shared. She wondered how much more she could discover, some maybe less secret, but just unknown.
With the key, she undid the padlock at the front of her crotch. When she’d been waiting for him to return home, all she’d wanted to do was get the key and hide somewhere, the bathroom perhaps, where she could take off this outfit. Now, she did not run, but pulled the leather tongs from between her buttocks, baring her pussy completely. She undid the buckle in her lower back that held the leather straps that circled her body, baring her breasts as they unwrapped. When she pulled the collar over her head, removing the harness completely, she stood naked in her friend’s living room. With just a burning red bottom to remind her of what had happened.
“I hope this wasn’t the last time I’m allowed to wear this, Sir.” She said, while handing it over to him.
Matthew smiled. “I usually only let girls wear this when we’re serious, a few dates at least.”
Jessie licked her lips. “If going on a date with you is what it takes, I guess it’s a price I’m willing to pay.” She teased.
Matthew grinned. She wondered whether he’d felt any uncertainty when telling her this or had just known what her answer would be.
“Talking about prices to pay.” Matthew said. “There’s one more thing I want. Some way for you to prove what an obedient girl you can be.”
Jessie blushed as he stepped forward to kiss her, pulling her naked body into his arms. He was surely confident about this and she melted away in his arms.
“Wait.” She said as he undid his pants, freeing the erection she’d felt pressing against her lower belly. She turned around when he stopped, placing her hands on the couch, her legs spread and red bottom up in the air, just like when he’d spanked her. “Fuck me like this, Sir.” She said.
Matthew slapped her bottom with a full-handed swat. “Stay!” He said, before quickly running up the stairs at the end of the living room.
Jessie wondered whether she’d been too forward. She was supposed to be submissive, not demand in which way he’d fuck her. Yet this had been al she could think of while he spanked her; when she’d discovered the leather outfit did not cover her pussy completely.
When Matthew returned, he did not carry another implement from his chest however, as she had feared. Instead, he’d gotten a condom and pulled it on as he stepped behind her.
Jessie moaned deeply, even before she felt his hands on her still sore bottom. She moaned deeper when his thumbs pulled her lips aside and he shoved his cock inside her.