Painful Pleasures


Warning:  This story is intended for Adults.  Drugs and sexual stuff.


“You lied to me.”

“I didn’t lie!”

“Don’t even try that, you said that the pills and weed weren’t yours and they clearly are.”  Before I could speak, Aaron held his hand up and said, “I don’t want to hear technicalities, Penelope.  I want to know why you think it’s okay to bring this mess into my home.”

I stared at the wooden floor, chewing on my lower lip as I tried to think of an answer.

“Look at me, Young Lady.”  When I didn’t move, he grabbed my chin and forced me to look up.  His brows were furrowed, jaw tight.  

“I don’t know.”

“You don’t know?  I’m with the FBI, did you think I wouldn’t find out?”

“Well, yeah…”

Apparently, that wasn’t the right answer.  “You are to be completely drug-free while you live in this house, do you understand?  We’ve already been over this before, it’s in the contract. I have a zero-tolerance policy.”

My eyes rolled, though I didn’t mean to and instantly regretted it when I saw his arms fold.  “Sorry, I just… weed isn’t actually a drug and Adderall is legal so…”

“You know what, this isn’t working.”  He glanced around the room, eyes landing on the straight-backed armless chair in front of the large oak table.  Then his fingers wrapped around my upper arm and he jerked me forward, leading me towards the chair.

I immediately started fighting.  “Wait, what? What are you doing?”  I tried to fall out of his grip, or somehow resist his tugs, but of course, that didn’t work.  

“Something you’ve been needing for a while.”  He pulled the chair back and sat, throwing me over his lap with ease.

My legs kicked up and I squirmed.  “Nooooooo… c’mon, don’t do this…”

“You should’ve thought about that before you broke the rules.”  I was wearing thin pj shorts that barely covered anything, so when his large hand descended on my backside, I felt it and yelped like a puppy when you step on his foot.

“Ouch!  Owwwwiiieeeessss!  Please stop!”  

I wasn’t used to being spanked by someone with such a strong hand.  Each swat stung like an actual punishment, suddenly transforming me into feeling like a kid over her father’s lap.  Fear spread through my body because I knew this wouldn’t be over until he decided it was.

“Do you think this is funny?”


“Excuse me?”  He landed a couple of swats on my bare sit spots which caused me to shriek.

“No, Sir!” I nearly howled, reaching back to block.

He caught my hand and pinned it against the small of my back, landing a few more stinging swats.  “I don’t care if it was ‘just weed and Adderall’… weed isn’t legal in this state yet and even if it was, you aren’t old enough.  And the prescription isn’t for you, therefore it’s illegal for you to have it.” A few more swats landed, this time on my sit spots and I kicked a little, peeved that I couldn’t move my hands to block.  “You’re in for a long and hard punishment, little girl, until you really and truly understand that drugs are prohibited.”

“But I do understand.”

“Not until you’re sobbing your eyes out.”  With that he tugged down my pj shorts and panties, then shifted my position so he could throw a leg over mine, preventing me from kicking.

“Don’t do this, please…”

“Oh, this is going to happen.  And if I ever find out you’re breaking any laws again, I’ll not hesitate to take this belt off and blister your ass.”

“Please no!”

“What are you going to do with the weed and pills?”

I didn’t have much of an answer for that, because I planned on just smoking it and taking them… but I couldn’t say that to him.

He knew that’s what I was thinking, though, and landed a barrage of spanks to my already-aching bottom.  I squirmed and tried to dodge the swats, wiggling my butt as much as possible to throw off his aim. He had a tight grip on me, arm circled around my waist, still holding onto my hand and had my feet locked in.  Every swat seemed harder than the last. He covered my bottom from the tops of my cheeks, all the way down to my thighs. He spent a significant amount of time landing punctuated smacks to my sit spots, claiming that he wanted me to feel this every time I sat for the next couple of weeks.

“Owwwwwww pleaseeeee I’m sorryyyy I won’t do it again!”

“Should I believe you?”

“Yessssss, I’ll be a good girl!”

“No you won’t.”  I felt his hand slap against my thighs.  “You’re not sorry because you’re not crying yet.”

“Pleaseeee don’t make me cry…”

“I’m not stopping until you’re sobbing,” he reminded me.  Then, without warning, started spanking really hard and fast.  

I writhed and bucked up, trying to break free from his grip.  My struggles just earned me harder spanks on my thighs, even sometimes my inner thighs, which just made me howl more.  I was still begging and struggling, much to his dissatisfaction.

That’s when he reached for the paddle.  It’s not too big, not too small, maybe about eight inches long and four inches wide.  It has eight holes drilled into it and is quite thick and heavy. I knew that piece of wood would make me cry.

“Noooooo, don’t use that!!”

In response, he popped the paddle down on my bare, unprotected bottom.  If I thought I was in pain before, the paddle swat had me near tears almost immediately.  Then he brought it down again, and then again without giving me a chance to breathe, and then again!  What the hell! He kept cracking it down on my bare bottom. The sound was deafening. My bottom must have been so red by then, it certainly was hot and sore.  Then he twacked the paddle against my sit spots and gave me a flurry of hard spanks, and it finally broke me. He reminded me not to have the weed or pills again.  I didn’t even argue with him, I didn’t even want the damn things anymore. My ass hurt too much and I was one sore, sorry little girl.

When I was sobbing like he’d wanted, he lifted me up.  But he didn’t hug me like I’d expected, I didn’t deserve that yet.  Instead, he put the hard wooden chair back in front of the table and gave me an essay to write.  The paddle sat on the desk in front of me in case I needed a reminder to keep working. It was torture, and I squirmed the whole time!

When I finished the essay, my butt was hurting more than ever, but instead of finally letting me rest, he decided that I needed another round.

He flipped me back over his lap, tugged my pjs down again, then started spanking away.  Within no time I was crying again, bottom re-ignited. He decided to make it even more painful when he pried my legs apart, causing me to straddle over his knee.  At first, I thought it was going to be sexually pleasing. But then he started swatting me on my inner thighs and that hurt like a bitch! I hated him so much right then!

For some reason, my body enjoyed the pain and Aaron’s assertion of dominance.  I didn’t want to! But I couldn’t help it… and I couldn’t hide it either.

When he noticed the liquid seeping from between my legs, the spanking stopped for a moment.  His fingertips brushed against my thighs, then crept towards the opening between my legs. They explored inside of me, properly lubricated.  “You’re liking this too much,” he admonished.

“I’m really not!” I promised, though at the moment his thumb touched my most sensitive area and a moan escaped from my lips.  Maybe this part I liked a little.

He tickled me until I couldn’t stand it anymore and quivered in pleasure, then I was still over his knee.

“Good.  Now you’ll be able to feel it again,” he said, removing his fingers and putting me back over his knee in a locked position.

“Wait… nooooo…” I begged, too fatigued to fight.

He landed a flurry of swats, hard and fast, covering my entire backside and making sure that it stung extra.  He ended with a couple dozen swats to the sit spots, then pulled my panties and pjs back up. I was a sobbing mess.

He lifted me into a hug in his lap, rocking me for a few minutes while I rubbed my throbbing backside.  “Time for bed, little one.”


“Do we need to have another talk?”

I whined, but insisted that we didn’t, then trudged to bed, butt still on fire.  And then I went ahead and had a little of my own pleasureful fun, enjoying the sting in my bottom and the fear I’d experienced.  That love-hate relationship I had with making people angry. I almost wanted to get more drugs just to piss him off again and see how far he’d go… would he actually whip me with his belt?  That thing was thick… it would hurt like hell! I’d definitely not be able to sit for a while, especially if he whipped my thighs.

My imagination ran wild, wondering what would happen if he caught me self-pleasuring after the thrashing he just gave me.  Would he fuck me? Or would he spank me again? Or both?

That idea was all I needed to finish, and then I drifted into a lovely, warm-bottomed sleep.

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