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.
