“Oh yeah, you little slut, take it! Take it all the way, you filthy little tramp!”

Cuckold MILF Stories: Housewife Goes on a Date With Her Stepson’s Bully

Those were one of the many obscenities my stepson’s bully, Sam, shouted at me as we fucked. I lay on my back, his sweaty body hovering over mine. He was smiling at me every time I looked up at him, knowing he was fucking the stepmother of a kid he went to school with.

My stepson lived the basement of the house which was soundproofed for his sake – he tends to get loud when he’s playing video games with his friends. To my benefit, this made my stepson oblivious to the fact that his bully was fucking his brains out one floor above him.

The flirtatious look we gave each other seemed so innocent at first. It didn’t take long for Sam to formally introduce himself to me, coming on to me from the get-go. I blushed when he told me that he was single, and wanted to take me out on a date.

At first, you might be judgmental about me going out with a kid my stepson’s age, but take into account that Sam and I were both adults. What we were doing might have been immoral, but it certainly wouldn’t have been illegal.

Sam was a tall guy, about 6’2″, really short hair with a babyface and a bulky athletic body. His chest pressed out against his t-shirt, and I would be caught many a time staring at his hulking body. He always seemed to be sporting a bulge in his pants when we talked.

My stepson’s jaw dropped when I told him I was going out on a date with the neighborhood bully. I didn’t want him to ruin the night for me, so I told him we would talk about it later before Sam and I left the house. I wonder if my stepson saw Sam squeeze my ass as we walked away.

Sam fucked me in the backseat of his car on our first date. He fucked me harder than I ever had been fucked before. The neighborhood bully called me every name in the book while thrusting his oversized cock and out of me. I moaned, screamed, and shouted his name. Honestly, he was the best lover I ever had. His car windows were wide open, which meant anyone who was directly outside the house could hear what was going on.

“Fuck, you’re wet,” My stepson’s bully snarled.

“This is what you do to me, Sam.” I groaned as his thick, dirty fingers explored my pussy. All I was to him at this point was another notch on his belt. It hardly mattered that I was several years older than him.

“You want this big cock, babe?” he snarled as he unzipped his zipper and shoved down his jeans.

“Please,” I groaned as he ripped off my dress. I couldn’t take my eyes off the enormous bulge in his boxer shorts. “Make a woman out of me.”

“Like what you see?”

“God yes,” I groaned. “I will worship it. Let me make love to that enormous cock in a way no girl ever has.” I pleaded in a voice I didn’t recognize.

Sam pulled down his boxer shorts.

“Fuck….” I groaned as his big dick bounced out of the elastic in his underwear. It was almost the width of my wrist, thick as hell.

“Suck my dick, baby.” The big cock bully commanded, pushing me to my knees.

Using both hands to hold it, I dropped to my knees and began licking all over the massive cock of my stepson’s bully like an ice cream cone. I knew he wasn’t pleased with my effort. He was getting aggressive with my hair in his hands, and soon began face fucking me, causing me to gag. As terrible as I was doing, I was in shock at how big this kid’s dick was. At least half bigger than my ex-husband’s, or any other boyfriend I had before him. Suddenly, he used one hand to pull me up by my arm and the other hand to push me back. I fell on my back on the desk behind us. Sam then spit on his hand and began rubbing my already-wet pussy.

“Gonna fuck you, baby. Gonna fuck you real hard,” he said through clenched teeth as he lined his enormous cock up to the entrance of my pussy.

“Make me yours,” I begged the big bully. “Go slow though. You’re too big…”

“It’ll fit.” He chuckled confidently. “It’ll hurt at first, but you’ll get used to it. All girls eventually do.”

“Oh god, it’s huge…your cock is so huge…” I began cumming as soon as he got the head of his dick inside me. Then suddenly, he pulled out.

“Who owns this pussy now, babe?” The bully taunted me with a smirk on his face.

“You do.” I caved. “Now please, fuck me. Fuck the shit out of me!”

And just like that, I was another notch on Sam’s belt. Before long, Sam took his cock out and sprayed my face with it after making me cum a few times.

When my stepson came out to get the trash the next night, his jaw hit the floor as he could see my bedroom from the window outside. He was speechless watching Sam fucking me doggie-style against the window. My hands and face were pressed against the glass as Sam’s hands squeezed my ass and thigh. His gonzo cock, about 9 and a half inches, was the thickest dick I ever had inside of me. I screamed out the bully’s name as my stepson walked away with his head down. Sam and I both laughed out loud before he pulled out, pushed me to my knees, and soaked my face and hair in his salty white cream.

The day after that, I walked in on Sam slapping my stepson in the face. I couldn’t hear what Sam was saying to him, but could only see my stepson nod in agreement every time Sam finished a sentence. Sam opened the front door for my stepson, but as he walked out, Sam’s big boot literally kicked his ass, making the boy fall to his knees. Sam laughed out loud as he slammed the door, walking back to where I was.

“Hey baby, you should have seen what I just did to your stepson!” Sam said to me.

“I did, kind of,” I responded. “What was that all about?”

“Well, he and I had a long talk, and we agreed that he should be my personal assistant.”

“What? What do you need a personal assistant for? You’re 19!”

“I don’t know. Sometimes I’m too lazy to do my laundry. Now I won’t have to!”

“Sam, that’s humiliating! He agreed to this willingly?”

“Not exactly, but he’s going to do it.”

“Of course he is. He’s intimidated by you.”

“What a fucking wimp. I wasn’t even that serious; I was just joking around, just picking on him, you know? Halfway through pushing him around, I realized that I could get away with him becoming my little bitch! What kind of man is he?”

“Honestly, Sam, I don’t know. I didn’t know he was so…submissive.”

“Well, he obviously gets off on younger dudes fucking his stepmom, or else he wouldn’t be so obedient to all of this. Most guys would have packed up by now.”

“I guess he isn’t like most guys, Sam.

“Yeah, no shit. Now shut up and suck my cock.”

Stepson's Bully Fucked Me in Front of Him
For more pictures in this series see “Cherry Pop“.

And I did. I got on my knees and sucked him off like a woman possessed. Turns out I was loud when it came to sucking big dick. Sam loved every minute, smiling down at me and slapping my cheeks for encouragement. He moaned, he laughed, and he screamed as he pulled my hair and shot his load all over my face. He gave me another smile before he pulled his pants up and walked out the door, telling me he’d be back in a few hours.

Husband Pisses His Pants Intimidated by Ex-Wife’s 19-Year-Old Boyfriend

I was hanging out with one of my girlfriends, Anna, by the pool later that day. I told her all about the past several few days, talking in detail about how I became a sucker for Sam’s cock, literally and figuratively. I told Anna how I loved worshiping the neighborhood bully, how the fantasy only got better by the fact that Sam had a huge cock. I even told her that his good looks were icing on the cake for me. I bragged to Anna about the fact that this young buck gave me more sexual satisfaction in the last few days then when I was married. Anna had no qualms about telling me how jealous she was since she was still married, and the sex had fizzled out between her and her husband.

A knock on the glass door interrupted our conversation. Sam walked in through our unlocked front door before introducing himself to Anna. I could tell my girlfriend was quite taken with the neighborhood bully, and Sam could see the way she was fawning over him. Her eyes went to his crotch much like mine often did – it’s kind of hard not to notice an enormous bulge coming out of a big guy’s crotch when he’s standing in front of you. Anna was laughing at everything he said – Sam had her right in the palm of his hand. I knew it was just a question of time before she was going to experience the bully’s big cock like I did. Suddenly, I became the jealous one.

My stepson and his father – my ex-husband – suddenly walked out and was surprised to see the three of us there. I had forgotten that he was coming over to discuss an adjustment for my alimony payments.

“Take a hike, fellas,” Sam said to them making both Anna and I moan, turned on by the alpha male’s assertiveness. “The grown-ups are talking.”

I watched my stepson squirm and make a fist when suddenly, my ex-husband stepped in front of his son to protect him from the young bully.

I walked over to Sam and told him to cool off, as we didn’t need to make this an uncomfortable situation. Sam chuckled and whispered in my ear that he was going to show us all who was the man of the house now. He then grabbed me in his arms and French kissed me right in front of my stepson and his father. With his tongue still in my mouth, Sam squeezed my ass as hard as he could. When he broke the kiss, he gave me a wink, which told me he was about to do something big.

“Just so you know, I’ve been fucking your ex-wife senseless, bro,” Sam aid to the man I once was married to.

“What has gotten into you? My ex-husband said looking over at me.

“Watch how you talk to my woman, dipshit,” Sam said to him with a tone.

“We’re leaving. Let’s go.” My ex-husband said to my son. Though I needed to talk to him, my ex-husband making himself scarce at that moment was for his own good. Sam had other plans for him, though.

“Why? Don’t you want to see your ex-wife get pounded by a real man?”

“Not really, Sam,” My ex-husband said attempting to stand tall against the big bully. I was proud of him but also knew he wouldn’t stand a chance against Sam, physically. “Listen, I’d appreciate if you’d leave instead. I need to talk to my ex-wife about a few things.”

“Nah, I’m not leaving,” Sam said defiantly.

“Fine, I’ll come back later. Let’s go, son.”

Sam walked right up to my ex-husband and shoved his chest as hard as he could. My ex-husband’s back was against the wall as Sam got right in his face.

“I didn’t say you can leave yet, sissy cuckold,” Sam said with a smirk. Anna and I swooned in the background knowing that the house we were in was completely paid for by my ex-husband. He was getting bullied by a kid half his age in his own house.

“I’m sorry Sam, I’m sorry. I’m so sorry.” My ex-husband squirmed. As hot as it was, it made me think of him even less than I already did.

“Louder,” Sam ordered.

“I’m sorry! Sam, please don’t hurt me!”

“Louder, bitch. Your ex didn’t hear you!”

“Sam, I’M SO SORRY, PLEASE DON’T’ HURT ME!” At this point, my stepson had his head down, completely embarrassed for his father.

“You need to show me some respect from now on, wimp.” Sam continued to belittle my ex-husband. “Now, just for that pathetic little outburst, you and your spineless son are going to have to sit in this chair and watch me pound your ex-wife. I want you to hear every word that comes out of her filthy mouth. Do you understand me, you sissy cuckold?”

“Loud and clear, Sam.”

“Say loud and clear, SIR. Say it.”

“You’ve got to be kidding me.”

SMACK! Sam slapped my ex-husband hard across the right cheek, making my stepson shriek in fear. A wet spot formed in my ex-husband’s crotch and ran down his leg.


“Good. You see this big dick of mine?” Sam asked grabbing a handful of cockmeat. “You are going to watch your ex-wife deepthroat it, take it between her tits, and then take it as far as she can in her tight little pussy. Her friend here is going to lick my balls while she’s doing that. And your son is going to film the whole thing, aren’t you buddy?”

“Yes, Sam…er…Sir.” My stepson obediently replied with his head still down.

Sam grabbed my ex-husband’s hair and threw him into the chair. I had never been so turned on before in my life. I came without touching myself watching Sam decimate my ex-husband and my stepson.

“Like father, like son, eh?” Sam chuckled before making his way towards Anna and I. “Come on, ladies. Let’s give these wimps a show.”