Stephanie and the Boy

Shooting Graham a smile over her shoulder, Mistress turned and gestured to her collection of paddles in the cabinet.

"Pick any paddle you'd like, Graham. I can assure you that they all hurt."

"Of course," Graham smiled, leading me over to the cabinet. Graham and my Mistress seemed a lot more upbeat than I would have imagined. It made me wonder just how long they'd been watching Tanner and me. Every Friday, when we would wait until we were upstairs to embrace, they knew. I wondered if they'd made bets over their drinks about when it would happen, planning out how they would punish us. I felt duped on all fronts.

A deep voice thrust me from my thoughts. "Eyes up, Stephanie. Tell me which of these paddles hurts most."

Lifting my eyes slowly to his under my lashes, I glanced over to the shelf Graham pointed to. Mistress never allowed me this close to her cabinets. There were paddles and canes and floggers that I'd never even seen before. My eyes widening, I took in the close to ten paddles varying in size and material. Graham must have noticed my surprise.

"You have tried them all, haven't you?"

"No, sir."

As Graham's lips turned upward, I couldn't help but think of how handsome he was. His smile was ever immaculate, and his dark beard framed it perfectly. His broad shoulders alone could take control of a room. I started to think that I wouldn't mind his hands on me...though as he was Tanner's dominant, I'd suppressed these thoughts before.

"That's right," he chuckled. "You're a good girl, aren't you?"

"Yes, sir."

"My Tanner has seen all of my paddles...and I'm sure that after today, you understand why. He can be very disobedient."

How had I not realized before? Every time Tanner had placed a hand on my thigh, I'd assumed he was being friendly. Every shy glance, I assumed was innocent. As Graham spoke to me, it became increasingly clear that Tanner had been drawing me into his trap.

"Yes, sir."

Graham paused to take in my expression. After a moment, he cleared his throat and continued, "Stephanie, I know that your Mistress has taught you manners. You should know not to touch things that don't belong to you."

My breath caught in my throat.

"Yes, sir. I'm sorry, sir," I whispered. I was shaking then, afraid of his harsh hand I'd heard stories of.

Graham took a moment to regard Mistress's paddles. He ran his hand across a few, deciding on one with a pink ribbon. He lifted it from the shelf, rotating it in his hand to admire it. There were hearts carved into the middle of the paddle which would leave heart-shaped markings on my ass. This one I'd experienced before, one day when I wore the wrong butt plug to Mistress's house.

"How does this one sound?"

Again, it struck me as odd that Graham was asking me my opinion. My Mistress would never ask how I felt about her choice of punishment, only if I accepted. It was interesting to see the differences in her and Graham's manners of dominating. I tilted my head to the side, a frown on my lips. I didn't know if he wanted me to actually respond.

"Stephanie. It's rude to keep me waiting for your answer."

"Yes, sir," I rushed out. Apparently, he did. "I'm sorry, sir."

"That's five extra lashes," Graham frowned disapprovingly. "I think that thirty-five is a good number. So, forty in total. Do you accept?"

"Yes, sir," I gulped. Hopefully, he wouldn't be paddling me at full intensity. Though my Mistress certainly had a strong hand, I'd never even experienced the full extent of her punishment...let alone this large man's.

Graham walked to the bed in the center of the room, taking a seat. I was close behind him, my arms linked behind my back submissively.

"Well, over my knee."

Obediently, I laid over Graham's knee. I'd never had a man punish me and wasn't exactly ready to start.

The first crack came quickly. It covered both of my cheeks. It wasn't very hard, but I knew he was just warming up. The next four came in succession, two on my left cheek, and two on my right.

By number twenty, I was crying. Graham slipped off my panties to place them in my mouth. The taste of my arousal filled my mouth, and I noticed just how wet Graham's punishment was making me. The sounds that Tanner was making across the room were not helping either. A part of me enjoyed hearing him be punished for deceiving me.

"Quiet, Stephanie. We're halfway done."

I nodded my head, bracing myself for the next swish of the paddle. These were harder, more direct. Graham was trying to leave an impression. By thirty, I was screaming. My panties had fallen to the floor wet with my saliva. My ass was burning, and I didn't know if I could endure ten more.

Graham groaned. "Your ass looks so beautiful with these hearts all over it. Maybe one day, your Mistress will let me use it."

I shivered at that thought, the thought of my Mistress letting him use me. I wondered if he was looking at my plug.

My pussy was becoming wetter with every passing second. Now that I focused on it, I could feel a hard presence under my stomach. Was I making Graham hard? Trickles of liquid were running down my leg and I couldn't even bring myself to feel embarrassed. I was a slut.

"Ten more," he grunted. Now, his voice was deeper, his arousal becoming more and more obvious.

"Hold on, Stephanie. I'm not going to go easy."

I knew that Graham was a lot of things, but a liar was not one of them. I braced my hands on the ground for the last ten thrashes.

Three cracks, one after the other, hit my left cheek. I screamed out at every one and had no time to recover before my right cheek received the same treatment. Graham was breathing heavily now, what with the effort he was exerting to punish me. I was obedient and kept my hands on the floor. Four more, and we'd be finished.

By the last crack of the paddle, I was howling in pain. Tanner hadn't lied about his dominant's hand. I was in a great deal of pain and it was barely offset by my arousal.

"All done," Graham spoke softly. "Come sit up."

As best I could, I sat up in Graham's lap. My ass already stung against his legs, and I wiped the tears from my eyes. After rubbing my back for a while, Graham stood me to my feet.

"Let's take off the rest of your clothes. You took your paddling very well, but I don't think your punishment is over."

I nodded my head, whispering a 'Yes, sir,' before pulling my shirt over my head. With his help, I slipped out of my skirt as well. Now naked, Graham took a moment to take in my body. I didn't feel self-conscious, but more...empowered. I liked that Graham was admiring my body.

"I see why Natasha won't share you, now," Graham chuckled.

I blushed, looking down before whispering, "Thank you, sir."

"And why she's so upset at my boy," he smiled. I could only blush in response.

He chuckled again, standing to his feet and placing his large hand against the small of my back to lead me over to the Saint Andrew's cross. Tanner was now unlocked from the fixture, standing next to my Mistress. His head was down, and Mistress stood proudly next to him. Tanner's eyes were red, and his face was still wet from his tears. He looked as if he'd suffered a lot more than I had. I also noticed that he had a ring around his penis, I assumed it was to keep him from cumming during his paddling.

"Give us a spin," Graham encouraged brightly. His tone was almost mocking.

The stripes covering Tanner's ass were vibrant. It looked as if Mistress had abandoned the paddle for the cane...or the tawse. Whatever she used must have felt like the devil's hand. I suddenly didn't feel so bad about my forty lashes. Tanner's tears and snot were streaked down his face and chest, and I couldn't help but feel bad for him. My ass was smarting, but not nearly as much as his must have been.

"Wow. Great work, Natasha," Graham complimented.

He couldn't have been more correct. Mistress had thoroughly taught Tanner his lesson, but I was certain that it was only an appetizer to the festivities to come. His eyes puffy and red, Tanner avoided looking at me. My heart ached for him. I wanted more than anything to run and comfort my friend, but I knew better.

Unbeknownst to us, Mistress had walked over to Graham to discuss their plan for us. Someone clearing their throat stole Tanner's and my attention from our pitiful gazes at each other. My Mistress was talking to us.

"--and since you two wanted to fuck each other so badly, we're going to let you."

Tanner and I looked quickly into each other's eyes, terrified by my Mistress's words. We both understood that there had to be a catch.

"Look at me when I'm talking to you," Mistress snapped, her tone offended.

Our reaction was immediate. Shivering in place, we whipped our heads around to watch my Mistress.

"Graham and I are being very kind to you. Do not ruin this opportunity for yourselves."

Graham looked from Tanner to me, raising his eyebrows.

"Well," he began. "Come here, Stephanie. Lay down over the bench."

As soon as I was bent over, restraints were being snapped into place around my ankles and wrists against the legs of the bench. The restraint around my neck wasn't fastened. I hoped that didn't mean that they would make me watch. I was ashamed enough.

To my surprise, Graham had Tanner stand behind me and he bent down to secure Tanner's ankles to mine. At the same moment, Mistress brought over a pair of handcuffs. Tanner's hands were cuffed together behind his back, leaving him almost unable to move behind me.

Tanner's cock stood hard from his punishment and I had to try not to twitch at the feeling of his manhood pressed up against me. Something told me I was unsuccessful, as Mistress was all but glaring at me in the mirror.

"Stephanie. Spread your legs, so I can lube your ass," Mistress spoke, pulling on the plug in my ass.

My eyebrows lifted in shock. I didn't think that Tanner would be in my ass.

Mistress must have noticed my expression because she scoffed, "Absolutely not. You thought that I was going to let this boy in my pussy? Spread, now."

That made sense.

As best as I could in the cuffs, I spread my legs as far as they would go. And with a swift motion, Mistress removed the metal from my body.

Replacing the plug were Mistress's cold, lubed fingers, spreading me in anticipation for Tanner's cock. There was something lascivious about that...my Mistress readying me for someone else's cock. Once she'd made it to three fingers, Mistress backed away to stand next to Graham. Mistress regarded us coolly. I wondered what our asses must have looked like, red, smarting, and almost pressed together. Tanner and I were both trembling hard.

Graham snapped his fingers.

"Go," he spoke.

As best as he could, Tanner pulled back until only the tip of his cock was pressed against my hole. He was very careful to make sure that it was the right one. I guessed that after his punishment, he understood what my Mistress was like when she was upset.

Slowly, Tanner pressed into me. His cock spread me gradually until I was stretched wider than Mistress's fingers. I could feel him throbbing in me, and it was a million times better than him being in my mouth. I could feel every ridge of his hard cock pressing into my wet hole, and it was enough to make me shudder. With every passing second, he pressed deeper into my quivering asshole until finally, all of him was inside of me. I gasped louder than I wanted to, avoiding my Mistress's eyes.

Almost as soon as he entered me fully, Tanner was pulling back to thrust back into my ass. He started a slow rhythm then, fucking me with his hips. I felt myself giving in to the pleasure, my hips rocking to meet his as best they could in the restraints. His cock was warmer and firmer with every pulse of his hips. Moans escaped my throat each time he pressed into me, all of my embarrassment from enjoying my punishment dissipating quickly. I had no idea how much I'd craved the moment...being connected to Tanner so intimately. We must have looked very funny, restrained and humping each other.

This went on for at least ten minutes. Tanner was moaning freely now, our sounds harmonizing with each of his thrusts. My head was resting on the smooth wood of the bench now. It was wet with my perspiration. Mistress knew how much I enjoyed bondage...as well as how much I enjoyed anal. I imagine that our dominants were very much enjoying the show. Tanner's moans increased in volume. I imagine that he was getting close, but he couldn't cum even if he wanted to.

Suddenly, there was a force pressing Tanner deeper into me. His balls pressed into my pussy, and I squealed, twitching against the wood. Squeezing my eyes shut, I focused on fighting my climax. I couldn't cum, not until Mistress told me I could.

A masculine grunt affirmed the presence behind Tanner, followed by a gasp from the latter. Graham must have pressed a finger into Tanner's ass.

"Ow," Tanner gasped. It sounded like he was on the verge of tears.

"Shut up," Graham scolded. "If you wanted more lube, then you should have thought about your actions earlier."

After a couple of minutes of accustoming Tanner to his fingers, adding more until Tanner was ready, Graham finally pushed his cock into Tanner's ass, making us a train of sodomy.

Graham's thrusts were much stronger than Tanner's. I felt them in Tanner's hips thrusting hard against my already-sore ass. I could only imagine what Tanner felt like. His ass was much sorer than mine.

"I thought I'd taught you better than this, slut."

Digging his fingers into Tanner's waist, Graham set a fast pace. With every one of his thrusts, Tanner's cock lurched deeper into my ass. Tanner fell forward and Graham pulled him to his chest. His submissive was screaming out in a mixture of pleasure and agony. I looked intently at the wall, my cheek resting against the bench. I was unwilling to watch my friend's punishment. If I could have moved my hands to comfort Tanner, I would have. This was my fault too; I should have been receiving the same.

Stern clicking sounded from the floor. Black heels walked into my vision and I felt a finger on my chin.

"Stephanie," Mistress spoke.

I looked to her eyes expectantly, despite the rough slap of Tanner's thighs against my own.

"Yes, Mistress," I gasped.

"Watch."

Reluctantly, I lifted my eyes to the mirror.

In the mirror, I watched as Graham thrust roughly into his submissive...fucking him into submission. Whatever sensations I felt from Tanner's cock in my ass were eclipsed by the sight of Graham ramming himself into the boy's tight hole. Despite myself, I grew wetter.

"Do you like watching your friend be punished?" Mistress's voice whispered in my ear.

I knew better than to lie and nodded, "Yes, Mistress."

In the mirror, I saw my Mistress smile before walking back to her cabinets.

A couple of excruciating minutes later, Mistress's voice returned from behind Graham.

"Graham, dear. You wouldn't mind, would you?"

I strained, trying to see what she was doing, but failed miserably. I couldn't see past Graham's body.

"Not at all. You are the lady of the house, after all," Graham smiled, stepping back. Tanner and I both took this moment to cool down before whatever else our dominants had planned for us. Our heavy breaths mixed together as he leaned forward onto my back. Sometime during this, someone removed the handcuffs from Tanner's wrists. I was almost jealous. My body ached from being in this position for so long.

"Tanner," Mistress commanded after a while. "We did not tell you to stop."

Standing back up, Tanner resumed his thrusts through his exhaustion. Finally, though, I got to feel his hands on my body. I imagined that if we hadn't been caught, this would have happened anyway, Tanner's hands on my hips, his pretty cock thrusting in and out of me. Moaning, I let myself be swept away by the feeling.

After a while, I looked up. Finally, able to peer over Tanner's shoulder in the mirror, I received the shock of my life when I saw my Mistress in her harness...wearing the biggest strap-on she owned. It must have been two-and-a-half inches in diameter and a foot in length. I was certain he couldn't take the huge cock. I gasped and Tanner must have heard because I saw his eyes widen. Tanner watched my Mistress in fear, starting to slow his pace. A sharp smack to his already-red ass corrected this.

My Mistress stood behind Tanner now, massaging lube into his already-stretched hole. He moved with her thrusts, thrusting into me. By the jolt of his hips, I assumed that Mistress had added a third finger to her two. A sharp cry and I knew it had to be four.

"Ooooh," Tanner moaned into my ear as he tried to keep up his rhythm, his thighs spasming every few seconds. Mistress's thrusts grew stronger, and Tanner and I both gasped loudly when Mistress's thumb entered his hole. I'd never had her whole hand in my ass, and my hole quivered at just the idea. I watched in the mirror as Mistress's wrist twisted deeper into Tanner's anus, probing and preparing him for her.

Withdrawing her hand, Mistress paused before thrusting her fist beyond Tanner's sphincter. I watched in awe. I remembered Tanner bragging about how much his ass could accommodate, but I never imagined this.

"Tanner," Mistress spoke firmly. "I'm going to teach you what happens when you try to seduce my submissive."

"Yes, Miss Natasha," Tanner murmured. Whatever rebellion he felt at the beginning of the night had been thoroughly beaten and fucked out of him by now. Mistress removed her hand from his hole.

"What do you say, slut?" Graham asked, sternly.

"Thank y--" Tanner gasped as Mistress thrust the huge cock into him. The next noise out of him was a piercing scream. His thighs shook uncontrollably, his body falling forward almost entirely onto mine.

"Thank you, Miss Natasha," he yelped, holding onto me for dear life.

At this point, Tanner no longer had to thrust, Mistress was doing the work for him. With every movement of her hips, the large cock drilled into his ass, pushing his sweaty hips into mine. Mistress was fucking us both now. It was a good thing the bench was screwed into the floor because if it weren't, my face would have been pressed into the mirror.

Tanner screamed in agony as the plastic cock pressed deep into his hole. I knew that my arousal was dripping down the back of my thighs then, I could hear it in the sinful sound of Tanner's thighs smacking against mine. In the mirror, Mistress held tightly onto Tanner's hips, thrusting the whole cock quickly into the small boy on top of me.

The next thing I noticed was Mistress, looking deep into my eyes through the mirror. Her mouth was curved into a focused scowl, her breaths labored. The sound of the metal shackles knocking into the wood was the only thing to be heard in the room. At that moment, it was just Mistress and me. I felt a shiver course through my body as her icy eyes burned into my own. Her message was clear. I was hers.

Soon, Graham's body eclipsed my view of the mirror. There was a thumb at my lips. He stood in front of me with his pants at his ankles.

"Let's see if you like sucking this cock."

This was an understatement, I learned when Graham dug his fingers into my hair and began to fuck my face. He slammed his cock down my throat at the same speed as Mistress's thrusts into Tanner. The combined sensation was enough to bring me to the orgasm I was holding off. I had no way to ask my Mistress for permission, nor did I have time. A rough slap to my cheek set me in motion.

Over and over again, I came on Tanner's cock. My scream came in waves as Graham's cock entered and exited my throat. I gagged, saliva gurgling out of the corners of my mouth. I was utterly fucked out, and my Mistress was far from finished.