Mama's Boy Ch. 01

Mama's Boy, Ch. 01

"Alright mom, I'm heading out for the night. I shouldn't be gone too long."

Mom sat on her bed reading a book, wearing her red night gown. She stared at me a moment before answering.

"Are you forgetting anything?" Mom asked, giving me a curious look over her reading glasses. I felt my pockets for everything I might need... keys, wallet, phone... everything seemed to be there.

"No... I think I have everything."

"Are you absolutely sure, young man? Sure you aren't forgetting anything that you promised you would do for me today? A certain... chore? Remember this morning in the kitchen?"

I instantly felt embarrassed.

"Mom, I'm so sorry! I totally blanked on that while I was getting ready for my date. I..."

"It's alright, we can just do it tomorrow."

"No, let's do it now. I promised you, and I want to do it."

"And be late for your date?" She raised an eyebrow.

"I don't care, I'll just text her quick and say that I'll be a few minutes late picking her up."

"Okay... if you insist, baby."

Mom sat her book on the nightstand and stood up from the bed. She undid the sash of her robe and let it fall to the floor. I took a moment to take in her glorious body before pulling out my phone and shooting off a quick text to Kelly, letting her know about the delay.

"Is this one sexy?" Mom asked, sauntering up to me as I completed the text.

"She really is."

"As sexy as me?"

Mom took my phone right after I hit send and placed it on the nightstand near her book.

"No, no one's as sexy as you."

"Good answer. You know how jealous I can get."

Mom pressed her naked body against me and we locked into a deep, sensual kiss. Our tongues fought against one another as we each tried to outdo the other's passion. Mom moaned as she felt my hands wander down her back to the wondrous curves of her ass. My middle finger even made its way into the crack of her ass, teasing at her tight backdoor.

"Mmm yes, that's what I want baby. My ass needs you. I'm desperate to get my ass wrecked by your big dick."

I spun Mom around so she faced the bed and firmly bent her down. She supported herself on both hands as she turned back to face me. Her plump ass beckoned me as my cock grew harder.

"It's okay if you want to be rough with me. You're in a hurry, so I understand if you just want to pound me, shoot your load, and get out of here."

"Oh I'm definitely going to pound you hard," I said, removing my shirt, pants, and boxers. Mom's eyes gleamed with lust as she took in the visual of my stiff cock, ready to pump her full. I grabbed the lube from the nightstand drawer and applied a good amount to both my cock and her waiting asshole. She squealed with pleasure as the cool sensation of the gel prepared her to be pounded.

"Yes baby, oh please just get it in. I wanted this so bad today. Cheryl was texting me about trying anal with her husband for the first time, and it just got me so horny to get assfucked."

I pressed the head of my cock to her tight hole, pausing for dramatic effect as she squirmed and pleaded for me to put it in.

"Oh my God, please don't tease me anymore. I need it. And you can't afford to waste any time right now, young man."

"I'll be fine on time. This is worth it."

I pressed into her, eliciting a long, low moan from my mother. She went silent for a few moments then, saying nothing but just breathing steadily, adjusting to the size of my cock up her ass.

"So big, honey... so big... every time... never get... ugh, never get used to it."

I pushed deeper until my cock was fully within the grasp of her asshole's vise grip. For a brief moment I thought I would shoot my load right away, but I fought back the urge and controlled myself.

"Mmm baby, you almost came, didn't you? I felt you tensing up." Mom grinned back at me wickedly, knowing how much power her tight ass had over me.

"I did Mom. So close."

"Good boy, showing so much control. And good thing I made you finish your chores, or you might have shot that load way too soon with Kelly."

"You're the best, Mom."

"I try... oh, oh yes, just like that, nice and deep. Fucking pound this MILF ass. Fuck your mother right up her tight backdoor. Such a... oh yes... such a lucky boy. Some mommies don't do this with their sons. Such a shame."

I continued pumping Mom hard and deep, interspersing my thrusts with the occasional slap on her ass. It was just so big and inviting, I couldn't resist the urge to spank it.

"Fuck yes, spank me. Spank me for making you late for your date. Punish me."

"Take that, you bitch. How does that feel, huh?" I gave her a hard smack on the ass, making her scream in addition to the grunts and moans she was producing because of the anal assault my cock was subjecting her to.

"Fucking slut, making your son late for his date just because you need cock. What a fucking whore you are." Another hard smack.

"Yes baby, I'm your whore, I'm just desperate for your cock and a thick load. Please shoot it up my asshole. Please, baby. I need it so bad."

"You want it now? Want me cum right in that tight little shit hole?"

"Yes! Yes! Let me have it, please. Cum in my fucking shit hole. Please, I'm begging you to fill my ass. I need it so fucking bad."

I lost all control at that point, exploding with several huge spurts into my mother's well-fucked ass. When I finished shooting my load, I pulled out of her with an audible pop and took in the beautiful sight of my cum leaking from her. Mom simply feel forward onto the bed, laying face down and breathing heavily.

"God, that was amazing. Thank you so much for that. I needed it."

"What about you? Let's get you to cum."

"Oh, don't worry about me baby. I need some more time to really build it up and you need to get going. I promise, it's fine. Maybe I'll take care of myself while you're on your date. And I will text you every filthy detail that's in my head while you're trying to talk with Kelly."

"You naughty bitch," I said as I gave Mom's ass one final light slap. I began to get dressed again, in somewhat of a hurry as I was now at risk of being late for the already-postponed date.

"Are you planning on bringing her back here?" Mom asked, looking at me over her shoulder as she got to her knees.

"Maybe. Do you want me to?"

"Of course. I love to listen. Like that last one you brought over, that really thick bitch... Ashley, was it? It was so great listening to you destroy her. I know she didn't walk straight for a week after that."

"Then I'll try and bring her home, if she's up for it."

"And you two haven't fucked yet?" Now Mom had turned to sit with her legs hanging off the bed, her glorious tits still heaving as she caught her breath.

"Not yet." I was now fully dressed, and I sent Kelly a text that I'd be leaving soon.

"I definitely want you guys here then. I want to hear her the first time she gets split open with that thick piece of meat. She might be too scared to take it up her ass, but that will come soon. If it doesn't, she's not the girl for you. I don't want my son dating a girl who won't take his beautiful cock in her ass. You need to be with girls who understands the requirements of dating a hung stud like you, and anal is an absolute necessity."

"Haha, I'll let her know you said that. But maybe that's more of a fourth or fifth date thing."

"Okay honey. Have fun on your date, and then bring her back her for act two. I'll make sure to be out of sight."

I gave Mom a quick kiss on the lips and turned to leave.

"And thanks for finishing your chores, baby!"

"Of course, Mom. Sorry I almost forgot."

Mom smiled at me with motherly affection as I exited the bedroom and prepared to leave for my date.

The dinner went well. Kelly is an easy girl to talk to and there was none of the awkwardness or lengthy strings of silence that can happen on some dates. At one point the topic of my mom came up.

"So if we go back to your place after this, do I get to meet your mom?" Kelly asked me with a smile. "It's usually a lot longer than the third date before I get to meet a guy's mom."

"Haha, I know it's not the sexiest setup in the world, but it works for us. We support each other and the house is big enough that we don't get in each other's way unless we want to."

"It's so rare to find a guy who actually admits he needs support! We all do from time to time, and I think it's great you're so comfortable and supportive of your mom. Family should take care of each other."

"Agreed. And to actually answer your question, no you won't get to meet her tonight sadly. She's out with friends."

"So that you can have the house to yourself when you bring your lady friend over?" Kelly gave me an exaggerated wink as she said this.

"Pretty much. Mom is good like that."

"That's great. I do get pretty loud..." Kelly said this last part without making eye contact, in a sort of stage whisper, while feigning sudden interest in the menu. I stared at her with what was probably a really dumbstruck facial expression until she broke her deadpan delivery and giggled at her suggestive comment.

"So," I continued, trying to change the subject back to dinner conversation, "what is sounding good to you?"

"I might just do a soup and salad. I kind of considered the steak, but... I know I'm getting a lot of meat later, so..."

"Wow, you are just in dirty mode already, aren't you?"

"I can't help it! I've heard about the... equipment you've got down there! Ashley never shuts the fuck up, so of course she talked about it when you guys hooked up. She said you almost broke her in half with that thing, and that you should need a concealed carry permit for it. I can't believe you put it in her ass, too..."

Kelly isn't great at controlling her volume, so our waitress heard all of this as she approached the table. She raised an intrigued eyebrow at me as she offered to take our orders. Kelly went first, ordering a light meal of soup and salad.

"And hey, Jenna," she added after she had placed her order, making a show of reading the waitress' nametag. "I saw that look. He's mine tonight, so don't get any ideas." This was said clearly trying to be more raunchy than serious.

"Also," Kelly continued, "could I get another glass of wine?"

"Of course, ma'am. Some more wine with your meal."

I placed my order, and the rest of the date went pretty much as expected -- some more small talk, a little more wine, and then it was off to my place for what I was hoping would be even more excitement.

Arriving back home, I was pleased to see a very faint light behind the curtains of Mom's bedroom window. She was probably in position on her bed, lying back and getting ready to play with herself. I had texted her that we were on the way back to make sure she was ready.

Mom's bedroom is just above mine, and her bed is situated so that she can hear me and the girls I bring over. My bedroom doesn't get much use unless I have a girl over, given that I spend most nights in Mom's bed.

As soon as we exited my car, Kelly came around the front and pressed me up against it, kissing me deeply and groping wildly at my cock through my jeans.

"So excited for this..." she mumbled as she kissed my lips, face, and neck. You could hear the tipsiness in her voice. "I could just suck you off right here to get things started. Would that be hot? Feed me my dessert load?"

"That's so fucking hot, Kelly. Let's wait though. Let's get inside. I want to see you better while you suck me." I kissed her some more and gently pushed her away, moving around her to unlock the front door and go inside.

Kelly dropped her purse on the living room couch and followed me into the kitchen. A bottle of wine sat perfectly in the center of the island.

"Oh my, well-staged! So you were planning on bringing me back and getting me drunk this whole time?" Kelly stared at me seductively as she stroked her hand up and down the bottle. "I love it."

"Just... planning for all possible outcomes."

"Smart guy... hey, I'm going to go freshen up in the bathroom. How about you open that and we can settle in for... phase two?"

"Sure thing. Bathroom is just around that corner on the right."

Kelly went off to get herself ready. I checked my phone and had a few messages from Mom.

All settled in here honey. Can't wait.

Hope you like the rioja I picked out for you two. It always gets me in the mood to fuck.

Wow! I thought she was going to suck you right in our driveway. Bad girl!

Look on your middle bookcase for a surprise.

Popping the cork on the wine, I poured two glasses and carried them into my room. I looked at my bookcase, and noticed a few things slightly out of position. Then I noticed the small, almost imperceptible red light peeking out from among the books. A camera! Mom was going to record this.

Making sure I still had time before Kelly got back, I fired off a text to Mom.

Camera? Can we watch later?

I got a quick response.

Sure. I will watch now though. Live stream 

Just then, I heard the bathroom door open followed by Kelly's approaching footsteps. I quickly put down my phone and flipped it face down on the night stand. Standing in the doorway, Kelly stared at me lustily while biting her lip.

"Mmm, there's what I want. Some more wine and some sexy man meat."

Kelly approached me and we kissed deeply. Breaking the kiss, I handed her a glass of wine and we each took a sip. She sat down on my bed, and I followed suit.

"Ashley told me a few interesting things about your hook-up, actually..."

"Like what?"

"Oh lot's of things... your size obviously, how you really took control and gave it to her rough... but what caught my attention most was about how much you cum."

"Oh? What did she say?"

"She said that she almost choked on your first load, it was so big. And Ashley has swallowed a lot of loads, believe me, she's not an amateur. She thought you just had a lot saved up, but she said your second load -- I think, the one that went in her ass -- was just as big. She said you flooded her and she was leaking for hours."

"Wow, she really doesn't keep anything secret, does she?"

"Ashley? Hell no. She never stops talking and things just naturally fall out. It really turned me on though, and I knew I had to see for myself after a few dates. I just love cum. It's like... I guess you'd say it's a fetish. I love swallowing it, tasting it, being covered in it... everything. And you sound like a perfect guy to help with that."

"I think I am," I responded as I leaned in for another kiss. Her hands groped me maniacally as she worked to remove my jeans. I did the same with her top. Soon we were both stripped naked and we stood admiring each other bodies for a few moments.

"Wow, that is... that is really something," said Kelly as she stared at my hard cock, reluctantly reaching out with one hand to touch it. "It's enormous... like... holy shit. I'm not even sure where I can put this monster."

"I have a few ideas..."

Kelly was stroking me know, mouth open in wonder at the size of the meat she was working with. I subtly took a few steps to the side, making sure that we were right in the field of vision for Mom's hidden camera. I gently urged Kelly to her knees and grabbed a handful of her hair, pulling her mouth slowly towards my waiting cock.

She looked nervously up at me as I entered her mouth. At first she was only able to take a couple of inches before she resisted my thrust, but after just a few tries she got about halfway down. She pulled off, gasping, leaving a hanging trail of saliva between my dick and her lips.

"So big... don't get any ideas about me deepthroating this thing."

"Mmm no, you're doing a perfect job. Your mouth is fucking amazing."

"Glad you like. Now give me some more of that."

Kelly plunged back down as far as she could on me, held the position for a few seconds, then pulled off and gave my whole shaft and balls an exquisite tongue bath, coating every inch of me with her spit.

"I'm a sloppy girl when I suck... is that okay with you, baby?"

"Fuck yeah, get it nice and wet like that."

"I love making a mess on a cock before the cock makes a mess on me."

I could only smile in response as Kelly went for another round of taking me as deep as she could. After a few more repetitions of this process, I was about ready to cum and I knew it would be a lot.

"Kelly, I'm... cumming... fucking cumming."

Kelly pulled me out of her mouth and started stroking me hard with both hands.

"Do it. Fucking cum for me right now. Burst all over my tits. Give me the load I'm waiting for. Fucking cum, right now! Do it! Shoot that big load for me!"

I groaned aloud as I felt my cock beginning to spasm. My first shot landed on her upper chest, just below her neck, and the rest ended up on her tits. In all I shot five big spurts of jizz, followed by a few smaller ones. Kelly stared up at me in shock.

"That... was... amazing! That's so much cum! Is that a normal load for you?"

"Yeah, pretty much."

"Did you cum before this today?"

"I did actually... had to calm myself before the date, you know?"

"Mmm... wow, so there could be even bigger ones than this. This is amazing. I love it. It's like I've been through a bukkake just from you!"

My cock had softened slightly, but it wouldn't need long to be ready for action. I stood watching Kelly scoop up bits of cum from her body and put it in her mouth, swallowing each mouthful with a smile.

"Tastes good, too," she added as she finished cleaning herself off. "Is that thing going to stay hard so you can fuck me now?"

"Won't take much. How about you lay back and let me get even for that blowjob?"

"I won't say no to that!"

Kelly got on her back and spread her legs for me, showing off her perfectly shaved pussy that was clearly already soaking wet. Kelly squealed with pleasure as I dove right in to the task, plunging two fingers into her as I began to lick her clit. It was only a matter of seconds before I added a third finger, given how wet and receptive she was.

"Fuck yes, that's it, that's it... right there baby... oh my God, yes that's the spot, right fucking there." Kelly began bucking her hips up into me lustfully. I tried to keep my tongue on her clit as she moved while still keeping up my steady thrusts into her pussy with my fingers. Feeling a little adventurous, I decided to playfully flick my tongue on her asshole a few times to gauge her reaction.

"Oh my God, you're tonguing my ass. Feels so good. Just tongue though. Don't think I can... oh yes, just like that... don't think I can take you in my butt tonight. Need to prepare for that monster."

I said nothing in response, just continued enjoying the pleasures of licking Kelly's tight little asshole before returning to her delicious pussy. My cock hardened further at the idea of fucking Kelly's backdoor, but I was fine delaying my gratification on that. After all, if I really needed to assfuck a sexy slut, Mom would be ready and waiting for me.

Kelly built slowly towards her orgasm, somehow becoming even more wet and slippery than she already was. Despite her growing pleasure, she gently pushed me away from her and motioned from me to stop for now.

"Your tongue is so good. Now get in me, I want to cum on that big dick. Put it in."

I straddled Kelly and did as she said, pressing the head of my cock several inches into her and eliciting a scream of pleasure. I pulled out, then repeated the process and pushed in further. Kelly's face was a rictus of pain as I pushed almost all the way inside of her. Her screams were replaced with quick, hyperventilating breaths as she adjusted to the girth of my cock stretching her open.

"Fuck yes! Pound that dick in me! Give it to me hard! Hurt me, baby!"