Disciplinary Pegging

Her footsteps got closer to me. The sound of her heels slowly striking the floor in my direction managed to excite and terrify me in more ways than one.

I had been kneeling down in the living room for thirty minutes as punishment from my stepmom. The coast was clear I thought. I could quickly masturbate I thought. My porn isn't as loud I thought. I thought wrong.

She used her spare key to open my room door and caught me oily handed and pants down. One hand stroked my rock hard cock while the other shoved a 4 inch dildo into my ass. She wasted no time pulling me to the living room, slapping me and forcing me to kneel while she searched my room.

Whatever the outcome of the search was, it wouldn't be pretty for me. She was quite prude and while she never had an issue with me having a relationship, she didn't have progressive ideas about sex.

"Oh, what do we have here?" She asked with a delicious voice. She brought forward her findings in a bag and I shook my head. I was fucked. She smirked at me as she placed them all on the table one by one. I bowed my head in embarrassment. "Oh, a whip, interesting. A pair of handcuffs, didn't know I had a criminal in my house." She chuckled. "Some beautiful riveting art, I didn't know you had this in you."

The art she was talking about was my main way of expressing my fantasy with my talent. I painted and drew smoking hot powerful women holding whips, blowing smoke and wearing strapon dildos.

Out of the art she found, I sincerely hoped there was a painting she didn't see.

"You even drew me? You're a thirsty artist!" She howled with laughter, sitting on the couch. "bend over like a dog, my feet hurt," she said and I did. Little did I know that sentence would have a different meaning later.

I drew and painted my mother wearing a red bath robe, her glasses and her brown hair flowing. She was draped with a pearl necklace (I had a jewelry fetish) and held a whip while putting a black rubber cock around her waist.

"I must say. For a horny pervert, you sure are quite talented." She mocked, pressing her legs harder onto my naked back. "Oh, and what's this... A strapon dildo. Looks much bigger than I'd expect you could take."

Indeed it was, both in girth and length. It was ten inches of thick titanium white silicone. I hoped one day I would find someone who would use it on me because I was too scared to use it on myself.

"Aren't we kinky, today?" She turned to face me directly. She only wore her red bath robe with a leather black bra and panties. She very much dressed like my fantasised portrait of her. She held my face and delivered multiple soft hits across it. "You know if your father were to see any of this. It would be game over, right?"

I nodded sheepishly.

"He's not been around for 6 months and this is what you do? I can't even imagine his outrage."

My dad was the standard middle-aged middle-class religious conservative. He usually freaked about how "woke" the world was becoming. I trembled at how he would react to it.

"Please, don't tell Dad."

She stroked her chin. "I don't know... he got me as a stepmom to watch over you since your mom left. He'd be disappointed if I let you off the hook." She smirked and picked up the whip. "Unless, you'd be down for some discipline." She leaned into my ears and whispered. "Your choice!"

I swallowed my spit and nodded. "Good choice." She stood up. "Kneel on the couch and place your hands on the wall."

I did accordingly, this punishment started to resemble my fantasy. I breathed and smiled. Whatever was going to happen wouldn't measure up to what my dad would do.

"Now if you're thinking I'm going to make this sexy in a way that's pleasurable to you..."

"Ahhh!" I screamed. The hit was much harder than I expected. Landing on my naked ass. Before I could catch my breath, she landed another three on my ass. "oh," it was painful. I didn't think it would be this painful when it was a fantasy.

She laughed out loud again. "You clearly don't know me. If you think this isn't going to leave marks all over." She swung the whip all the way from my back to my buttocks and even my feet. Giving me barely any room to cry before the next lash. "It would be very bad parenting if you enjoyed your punishment, don't you think. Oh no, I want you to remember this!"

She swung again more times. "oh, your hand is off the wall... Guess I'll have to start over."

"Please, I can't take it anymore." I whimpered, my smile from earlier was gone. "I promise I won't do it again!"

"Oh, I know and after now, I'll make sure." She chuckled inside her mouth, rubbing her nails on my skin. "Brace yourself for another round of your punishment! And this time I want you to count the strokes. We're going to 50!"

She started swinging again and I counted. "1, 2, 3... 24, 25." My eyes were bloodshot with the tears that soaked the couch. "40... Ahh!"

"Why'd you stop?" She leaned into me. "You know what that means."

"Please don't start again." I coughed.

"Starting again!" She continued, I stopped counting. She restarted until I could finally complete it. By that time, my back was nothing more than a pool of lines. She walked over to me and held my swollen face, licking my tears and kissing my forehead. "Awww. My poor stepson couldn't take a beating like a man." She teased.

I was beyond humiliated by my own whip. I fell down on the couch, everywhere I hurt. Ironically a weird pleasure came from the stings. Her dominating nature was a turn off but the beating kept my dick flaccid.

"I hope you know what's coming next?* She asked, throwing down the whip and picking up the giant strapon. "It's going all the way into your ass."

"I can't take it yet," I said. I bought that strapon for when my ass was ready, after I had taken smaller sizes. This was the grand finale.

"Well you're certainly gonna learn how to take it." She wore the strapon and licked her lips at my vulnerable state. "I've given you enough time to heal. It's best, you come over and suck this cock... don't make me use the whip."

I rolled out of the couch and knelt in front of her. My tears had already died out. Slowly I licked the tip and put it into my mouth, sucking it and putting my saliva on it. She hummed, nodding accordingly. With every second, I went deeper into the dick. Until it got to my throat and then she pumped it.

She held my head and stroked her cock into my mouth, making me gag. I didn't see it coming.

She laughed. "Nice how you were going slow but I need to up the tempo right now." She pulled my head back into the dick and forced it down my throat. I coughed and spat on the floor. She slapped me. "You spit on the cock, you understand?" I nodded accordingly.

She continued to violate my mouth, making me take the entire monster in my tiny throat. "Oh, you nasty boy. Such a slut you are." She smiled and forced my head into her dick, holding my nose and stopping my breath for a minute until she let go. I gagged so hard at the recoil that I nearly vomited. She, of course, enjoyed it.

"Okay now I want you to suck it all good. Because it's going up your ass now. I may not use enough lube for this cock so make sure it's wet."

I continued sucking her dick, going in and out as she moaned in my ear. "Nicely done. You ready to take this dick up your ass?"

I nodded.

She pulled me to the couch, lubed the dick with oil and bent me over like she did when she was whipping. "I'm going in." She went in slowly and I gasped once it went in. Much bigger than I expected.

"Ah!"

"Oh... you feel it?" She asks, pushing it in slowly. "You feel that big cock don't you."

"Yes."

"Say yes mommy." She said, spinning her hips. She gave a hard spanking to my ass and I whimpered. But it felt nice as she went slow, I could feel it hitting the spot.

But out of nowhere, she sped up. Giving me hard thrust after hard thrust. I screamed as she held my shoulder. "Awww baby boy. Did you think I was going to go easy on you? This is your punishment, have you forgotten."

"No!" I croaked as another stroke went in. She did it so fast and so easily like her waist had no bones.

"Yeah yeah! Take that dick! Take it all in that boy pussy!" She said, grabbing my waist and pounding the shit out of me. At least not literally since I had my ass cleaned. "Ohhhh you're not smiling now, are you?"

"No, mommy."

"Hahaha. How's that dick feel? You like this giant cock ram against your tight ass while you take it like a bitch?"

"Yes mommy!"

"Say it. You're a fucking bitch who loves cock."

"I'm a fucking bitch who loves cock!"

"Say it to the camera." She slowed down and put her phone in front of me, starting a video with the front camera and continued pounding hard. "Why do you like cock so much?"

"Cause I'm a bitch!" I screamed, as my ass got beaten harder than an mma fighter. I enjoyed it so much even though it fucking hurt. It hit the spot so well.

"I can't hear you!"

"I'm your fucking bitch, mommy!" I screamed again as the whip hit my back. She let go of my waist and was now swinging the dick entirely in me effortlessly.

"You like being your stepmom's bitch?"

"Yes I do mommy!" She continued to whip and pound. My legs and knees were vibrating. It was like I was having a million orgasms at once.

She paused. "Okay now I want you to fuck me back." She spanked my ass. "Come on baby boy. Back it up, back up on that dick."

I obeyed and pushed my ass deeper and deeper into her penis. She put her hands behind her head and smiled. As I thrusted myself into her, I moaned softly.

"You're loving this aren't you. Dirty dirty boy." She said and I smiled, it felt very nice. I even managed to chuckle. She held my neck and pushed it deeper into me, giving me a kiss on my forehead before she pulled out. "Come with me!"

I crawled behind her all the way to her room and she sat down on her bed. "Suck this cock."

I sucked the same way I did the first time and then she lay there. She told me to hold the iron bars on her bed and suspend myself in the air, facing the other side. "Now I want you to ride it. Like you never have. And don't let go."

I obeyed and from the bars I moved my ass in and out of her dick. She laughed as I did it, enjoying every moment. The camera was clearly facing us like before. I moaned more passionately. This position was much more pleasurable.

"You really are a slut are you? You're loving that dick."

"Yes mommy. I love it so much!"

"Promise to be better?" She asked and I agreed. "Yeah, you're a really naughty boy." She used the whip to flog my back hard as I bounced on it. My body sweat even more and it felt like my ass was going to burst open any time soon. "Yeah, you go, Cowboy! You fucking go!"

"Yes mommy, I will." I croaked as my dick got harder. I had to fight the urge not to touch myself but precum was already starting to spill.

She pulled me from the bars and onto my waist where she pounded me and stroked my penis as she railed me. "Oh yeah, you like that! You fucking like that?" She stroked it with the same momentum she used to fuck me and I screamed even harder.

"I'm going to cum, mommy!"

"Oh no you won't!" She let go of my penis and turned me around to face her, giving me a soft slap. She held my face, "you don't cum until I say you do. Okay?" I agreed and continued to ride her dick in a reverse position. She spanked me a lot harder this time. Almost every second I rose, her strong hands were smacking my soft ass cheeks.

"Spank me harder, mommy!" I moaned and she smiled, delivering it hotter and hotter. Her hand was going to be stuck on my ass for sure. She showed no mercy. Just the way I loved it.

She picked me into the air and bounced me on her dick as I grabbed her shoulder. I knew she was strong but I didn't expect her to be this strong. I truly was just a bitch at this point. No debates at all.

"You've never had a woman this strong life you amd fuck you senseless?" She giggled as I smiled back at her. Indeed she was fucking my brains out and I loved every minute.

She threw me back on the bed and took off her bra, exposing her huge boobs. "You can touch them darling. You earned it." She smiled, proceeding to piledrive the fuck out of me in missionary. I breathed faster, switching between laughter and tears as my shock waves fell through my body.

"You want me to choke you, baby boy." She asked as I squeezed her soft bosom.

"Yes, choke me mommy!" I begged as my eyes watered up. I was feeling everything. My head felt like it was always going to explode. Her constant dirty talk made it better.

She choked me with one hand and used the other to stroke my junk. "Yeah, oh you're ready to come aren't you, baby."

I nodded, her hand still firm on my neck.

"Yeah, beg for it. Fucking beg for it."

"Make me cum, mommy," I said faintly and she rested back and penetrated me, giving her more room to stroke it.

"AHHH AJMHJ AHANJDMIN OH MY GOOOOODDDDDD;" I screamed as I closed my eyes. "I'M CUMMMMINGGGGG!" My entire body submitted and I had the best orgasm of my life.

***

After a few minutes of me lying on the bed, holding my face as I recovered from what just happened. She stretched her hand and lifted me up.

"Normally I'd ask you to lick my pussy but you look beyond drained." She waved her phone to me and showed me the video. I felt embarrassed but more than that, I was thrilled. "If you misbehave again, I have this video. Always remember."

I whispered. *Thank you, mommy."

"You're welcome, baby. Now go shower please and get some rest," She said and I nodded. "Also don't expect to get any of your toys back again. They belong to me and you'll only use them when I say so."

"Okay, mommy." I said and walked to the bed. My whole body was lined, my ass was sore to the point I couldn't sit down and I just pounded senseless by my mother.

Best day ever.