Dude, You Slept With My Mom?! Ch. 03

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Most people have a bucket list; I have a Fuck It list.
12.2k words
4.82
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Part 3 of the 8 part series

Updated 04/27/2024
Created 08/13/2023
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~~~~~

Just a note: One of the moms - in this chapter - roleplays a mother/son relationship with Augie - during their intimate time. If this is going to be a problem for you, pull out now. Sorry.

Please keep in mind that, as this story progresses, we're going to get a few moms with different appetites. I'm not trying to give anybody PTSD here - I'm just attempting to give these 103 moms some variety.

~~~~~

~~~ Plans & Precautions ~~~

Emily and I lay in my bed, naked, talking. I was on my back; she was lying on my stomach, straddling me, looking into my eyes. My stiff cock was standing tall. Emily was twerking her tiny little butt against my rod - gently bumping & bouncing her labia, taint, and ass-crack against my prick while we chatted.

Actually, she was doing all of the talking. I was trying to listen while she was making my dick even harder - which was making it harder to listen.

"I already know everything I think I need to about you," she told me, "but I want us to get to know each other better."

"Your pussy & ass are stroking my dick. I'm not sure we can get much closer," I said.

"You know what I'm mean, Samuel Fowler. Tell me about me."

"You?" I asked, "You're cute. You have cute tits with the cutest little nipples. You have a cute little mouth that somehow fits over my cock."

"Not that stuff!" she complained, "Who am I?"

"I don't know," I said. "You're Emily."

"What do you know about me? What kind of person am I?"

"You're mysterious."

She sighed. I wasn't sure where she was trying to take this conversation.

"Who would Danny Fosdick say I was?"

"Danny Fosdick? Danny is a cunt. Not a pretty pink one that smells like honey; he's a festering green cottage-cheese cunt."

"That's gross! Why would you say that?!"

"Cuz you asked about Danny Fosdick and what he thinks. I don't care what he thinks. He's a tool. His mom's nice. He must take after his dad."

"You fucked Danny's mom?"

"Yeah. She was all hiding under the covers - being shy - and shit. When my cock-head bumped her cervix she wanted to know if she had it all inside of her. I laughed - and then she wanted to see. She threw the covers off to look cuz she didn't believe me. She's a good kisser. Once she had us uncovered, her shyness disappeared, and she turned into a wildcat. Wanted my ball-sac to slap against her ass when I fucked her - which obviously wasn't going to happen because she could only take half my prick - so I fucked her gap until she was ready to take my load and then I dumped it inside of her. She liked it. She said she was gonna get a big dildo and try to get me all the way in next time. She's got her work cut out for her. Her pussy's tiny."

"God! You're making me horny! Hornier!"

I reached down and gripped her ass-cheeks in my palms - grabbing on tightly - rubbing her cunt & ass-crack up & down my shaft.

"Will you stop that? You're supposed to be telling me about who I am."

"You want me to stop this?" I asked her.

"No," she complained.

I laughed.

"Shut up. You've got me all fucking hot now - and I need to cum."

"Oh! I'm sorry little stalker. Did I spoil your plans?" I asked her. "What are your plans anyway?"

"Fuck!" she gasped. Taking a breath, looking into my face, she said, "First plan is to cum. Second plan is to cum again. Third plan is to get you to cum inside of me."

"I like that plan," I told her.

I used my grip on her ass to drag her body a few inches lower - so that my prick was at a 45-degree angle - rubbing along her juicy quim more - bumping all of her naughty bits.

She shivered as the first orgasm hit, and exclaimed "Goddamn, you make that so fucking easy!"

I slid her up, across my chest, gave her a quick kiss, and then dragged her naked little elfin body back down mine until I was rubbing her business against my fuck-stick again.

She groped my chest a bit, with her hands, but then stuck her tiny fingers under me - between the mattress and my ass - trying to hold me in the same way that I was holding her.

"You're like a little fucking sexy Tinkerbell," I told her. "I could just plop your tiny little cunt down on top of my spunk-spigot and blast you full of cum."

"I may need to borrow Mrs. Fosdick's dildo for a while first," she admitted.

I slid her small body up mine again - capturing her lips with my own. Her tiny nipples raked against my chest. I pulled her up high enough to nudge the head of my cock into her small, tight entrance.

After a short, hot kiss, I dragged her ass back a bit until the head was getting ready to push inside of her.

"Fuck. Yes!" she moaned.

I moved my grip from her ass to her hips and slowly slid her body - and pussy - onto my penis - shoving it most of the way inside.

"You are so damned tight, Tinker!" I moaned.

"I'm not that tight. You've got a fucking intercontinental ballistic missile shoved up my twat!"

"You want me to stop?" I asked her.

"Not until I'm dead," she said. "Give me a little more."

I pushed her hips down until she had all she could take - stopping when the head brushed against her cervix. As soon as she relaxed, I rolled us over.

"Fuck! Yes! Now bruise my womb and fuck me full of your jizz."

I slid out of her pussy's tight grip - and then pushed in again - just bumping her wall.

"Harder," she ordered.

This time I pushed in until her tiny frame jolted a little.

"Harder," she demanded.

The third time, her body bucked a little when we collided.

"Yes," she said. "Keep doing that."

I fucked out of her - and back into her - over & over again - banging on her womb each time. She started flexing her channel on my prick as I drove in & out.

"Oh, Yes!" she said. "I've got one coming," she purred - as I felt the tremors start to run through her body.

I kept fucking her.

"Fuck! That's nice. Okay. Maggie said not to wear you out. Use me for your little cum-dump and then I want to sleep with this fucker buried in my snatch so I can convince my pussy to take more of you next time."

She curled herself in half and held the soles of her feet to the sides of her head.

I gazed down at her tight little body - in this super-erotic pose. I wrapped my palms around her ribs and started fucking her - banging my cock into her - pushing toward the climax that had been building.

Beneath me, she grunted and moaned as I battered the wall of her womb, relishing the amazing feel of her vaginal muscles gripping & grasping at my fuck-meat as it intruded & retreated. I felt her body starting to tremble once more - and hurried to try to cum along with her.

"Fuckkkk!" she cried out - as her channel gripped me even tighter - which sent me over the end.

My cock erupted inside of her as she lost her grip on her ankles. I grabbed them - continuing to hold her open - and further snugging the head of my cock against her cervix - as it belched load after load of my seed inside of her.

I repositioned her legs - back to normal - to see if her lungs would refill a little faster - then rolled us over so she wasn't supporting any of my weight. She was alert again a few seconds later.

She threw her arms around my neck and kissed me hard.

"Just like that. I may not be able to walk tomorrow - but that was perfect."

"You'd better be able to walk," I warned her. "We start on Elena Moretti's yard and Mr. Reynolds won't be happy if only one of us is working."

"Don't worry," she cooed, kissing me again, "I'll live - although I may need an Ibuprofen."

I groped her little butt-cheeks and then pulled the covers over us.

"Luca's mom?" she asked.

"Yeah. Said she'd rather ride her Harley than do yardwork. She said she was going to talk to Maggie about having us do it full-time."

"What was she like?"

"Tight body. Took most of me. Next time, I want to see if she'll wear her riding chaps."

Emily giggled at me and gave me a seductive kiss.

"Next time?"

"Maggie rewards them with more 'sessions' if they give us landscaping jobs - or get names scratched off of my bucket-list."

"Bucket-list or fuck-it list?"

"Either one," I told her.

"Maggie in love with you?" she asked me.

"I don't know. I've definitely grown to care a lot about her. She takes good care of me."

"Does she?" she giggled.

"Yes - that way too - but she's made this whole bucket-list possible - so I kind of owe her. She's fun to fuck. She makes you feel appreciated. I really can't believe all of this is happening."

"You okay with me?" Emily asked.

"Why wouldn't I be?"

"I didn't really ask you first."

"You gave yourself to me; I give myself to you. What's to ask?"

"My plans. I want a little more than just a nice fuck every once in a while."

"What do you want?"

"Your love."

"You already have some of that."

"Love or lust?"

"Both. You saved your cherry for me. How long did you do that?"

"A couple years."

"Longer, I think."

"Why does that matter to you?" she asked.

"I don't know - it just does. Why does it matter to you?"

"I don't know," she admitted, smiling. "It just does."

"That's why I'm not too worried about your plans."

"You're not?"

"Are your plans for us to be together and maybe make a baby or two?"

"Yes," she admitted, biting her lip.

"Are you going to change any from what you are right now?" I inquired.

"Do you want me to?"

"No," I told her.

"Then, no. I'm not sure I could anyway."

"Do I need to change?" I asked.

"No. Not at all," she said with certainty.

"Even what I'm doing with these other women?"

"You've been taking care of Maggie this whole time?"

"Yes - since our first time together."

"... and you have room in here for me?"

"I'll make it work."

"Then I only have one request - but you can think about it - it's a request; not a demand - and it doesn't have to be right now."

"What?"

"I would like a ring - just for me - you don't need to wear one. Maybe Maggie needs one too."

"You'd be okay with Maggie having a ring too?"

How long have you two been together?" she asked.

"A couple months."

"We'll talk to her and see what she says. I'd be very surprised if she wouldn't like to have a ring from you."

I nodded and pulled her in for another kiss.

She laid her head on my chest and we fell asleep.

~~~ Yardwork ~~~

Early the next morning, Emily & I met with Mrs. Moretti to go over everything she wanted done with the yard.

Once she had finished itemizing the tasks - and specifying how she wanted things done - and how they should look when we were finished, I admitted that I had no idea how long it was going to take. I offered to do the job for free the first time and then give her a quote once I knew what I was getting myself into. I warned her that I'd probably need Mr. Reynolds to look over my estimate before I gave it to her.

She went back in the house and we got to work. By lunchtime, we were wrapping things up, and she came out to chat as we were putting our tools back in the truck.

Looking at Emily, she said, "You had me worried a little - and I shouldn't have prejudged you - but I did. I apologize. You're a good little worker."

"Thank you, Mrs. Moretti."

"You in Luca's class as well?"

"Yes, ma'am."

She nodded and said, "If I steal this boy for a while when you come back to visit, is that going to bother you?"

Emily laughed and said, "He's already looking forward to it. Said he was going to see if he could get you to wear your riding chaps."

Her eyes turned to me and i felt my cheeks turn red. She looked back at Emily, reappraising her once more.

"He's a good ride - and seems to have a kind heart. Be good to him," she said.

"Yes, ma'am," Emily replied, smiling.

Turning to me, she said, "Riding chaps? Hmm. Can't say that I've tried that before. Get me that quote - but I doubt you'll be too expensive for me. I've seen what you do," she glanced at my tented pants, "and I like it."

She looked back between the two of us and said, "The yard looks good. See you kids next week."

She was halfway back to the house when she called out, laughing, "Make sure you're ready to ride when you come back."

~~~ Week 7 - Sophia Erickson (#11) ~~~

When I stepped into Maggie's bedroom, everything looked ready for another "session" - except that my "client" was still clothed.

"Hello, Augie," Alice Erickson said, somewhat shyly.

"Hello," I replied, looking over her body. She was dressed well - and had all of the MILF qualities I'd come to appreciate.

She let me look before we proceeded.

"I have a bit of a fetish," she admitted. "I like to roleplay."

"Okay," I said, looking into her eyes.

"I don't have a son but I've always wanted to do a mother/son thing. Are you okay with that?"

"Am I seducing you or are you seducing me?"

She clapped her hands together with glee. Her ample breasts trying to escape her blouse to demonstrate their enthusiasm as well.

"Me seducing you - at least this time," she said, grinning broadly.

"Undress now - or are you going to talk me out of my clothes?" I asked.

Her smile disappeared as she slipped into character.

"Augie?"

"Yes, mom?"

"You've spilled something on your clothes. We'll need to get those off before the stains set in."

"Oh! Right!"

I fumbled with the buttons on my shirt until she decided to step in.

"Here, let momma help you," she said, moving into my personal space.

"Thanks, mom. I'm such a klutz. First, I spill all over myself and now I can't even unfasten the buttons."

"It's okay, dear. Mommy will help you. Mommy likes to help."

"I like it when you help me, mommy."

"You do?"

I nodded, biting my lower lip. She took off the button-front shirt and laid it aside. She grasped the undershirt and pulled it up and over my head.

As it came free, I "lost my balance" and fell forward, catching myself by laying my palms on the front of her blouse - on her breasts.

She gave a little gasp.

"Oh! Sorry, mommy! Sorry!"

"It's alright Augie. I'm your mother. You don't need to apologize. A little touch doesn't hurt anything. See? We can touch."

She laid her palms on my pecs, hesitating a moment before she felt around my chest, swallowing the saliva that had accumulated in her mouth as her eyes went slightly out of focus and her mind lost track of what she was doing.

"So strong, Augie. Momma's boy is turning into a man."

"Will my pants stain too, momma?" I asked.

"Oh! Yes. We need to get those off. Here, let momma help you."

As she fumbled with the buckle on my belt, my cock got harder and harder - which flustered her more because she was focusing on the tent in my pants - rather than on the buckle. I placed my hands on top of hers and helped her unlatch the buckle. I expected her to look up - into my face - as my hands covered hers - but she was mesmerized by the outline of my phallus.

Once the belt was open, the fly unzipped along with the waistband spreading - and her hand shot down the front of my pants to clasp my cock through my boxers.

Our story paused while she felt me - measuring - assessing the girth - and then the length - her arm thrust into my jeans up to her elbow.

Picking back up on our roleplay, she said, "It doesn't feel like anything got burned or broken."

"That's good," I replied, trying not to smile or laugh.

"But, let's get these pants off to be sure."

I kicked off my shoes as she worked to get my pants - and boxers - to my ankles. My stiff cock bumped her cheek as she leaned down.

"Sorry, mom," I said - not sure which direction to take the dialogue.

"It's okay, Augie. Does it hurt anywhere?"

"Umm ..." Decisions, decisions. "... the end hurts a little."

"The tip?"

"Yes. A little."

"Do you think ...?" She licked her lips. "Would you like momma to kiss it - to make it feel better?"

"Yes, momma. Please, can you?"

Sophia's mom licked her lips, staring at my cock. Her hand came up to take hold of it. She pulled the skin back a little - and then stroked it twice. Her eyes were still locked onto the head. She leaned forward until I could feel her exhaled breath, bathing my cock-head in heat.

She didn't kiss it - well - I guess you could call it a French kiss. She stuck the head into her mouth and ran her tongue around the tip.

My balls ached.

She continued sucking - and stroking.

After a few minutes she stopped, looked up, and said, "Is that better?"

"Yes."

"How does it feel?"

"It's a little cold. Can you ...?"

"Yes? Tell momma."

"Can you rub it and make it warm?"

She stroked it a few times, staring at it once again. Spying a drop of pre-cum, she snagged it with her tongue, savoring it like it was ice cream on a warm day.

"Better?"

"A little."

"It's still cold?"

"Kind of."

She looked up and down the length - still holding it in her hand and said, "Momma has someplace warm we can put it - but you can't tell daddy."

"Okay."

"You promise not to say anything?"

"Yes, momma."

"It's warm inside momma's body. Would it be okay to put it in there?"

"It'll be warm?"

"Very."

"That sounds wonderful, momma. Can I put my thing in your body so it gets warm?"

Mrs. Erickson started ripping her clothes off and told me, "Lie down on the bed."

"Yes, momma."

She kept her bra on, climbed on top of me, and took my cock as far into her juicy twat as it would go, sighing as it touched her cervix. Reflexively, she rode it - up & down - for a half-dozen strokes - her eyes locked straight forward.

Looking down at my face, she said, "Is that better?"

"Much better, momma. It's warm in here - but it's still tingling a little from being cold. Can you rub it some more - like you were just now? That felt really good."

She pinched and squeezed her breasts - trapped in her bra - as she rode my cock.

"Can I hold onto you, momma?"

"Yes, Augie."

I gripped her hips as she continued to ride my prick - her talented twat gripping me as she fucked my dick in & out of her vagina.

"Momma?"

"Yes, Augie?" she answered - her eyes closed.

"Can I see your boobies?"

She peeled off the bra and threw it toward the rest of her clothes. I let my eyes devour her offering. Her D-cups begged to be held and her nipples pleaded to be sucked.

"Can I ...?"

"What, baby?"

"Can I touch them?"

She took my hands and placed them on her breasts. I groped them, squeezed them, pinched them, stroked them, and teased them.

"Do you like momma's titties, Augie?"

"They're really nice. Did I used to suck on them?"

"Yes, baby. Would you like to do that again?"

"Yes, momma."

She leaned forward until her left nipple went into my waiting mouth. I sucked hard - and then licked all around her nipple & areola. She moaned - and fed me the other one. I gave it the same treatment and she was practically purring.

I fondled her breasts and continued adoring them with my mouth as she rode my cock - stroking my meat-stick in & out of her gripping gash.

After about five minutes, I could sense that her orgasm was coming. I'd been staving mine off - to see what our next step was - but this would be a "one & done". I wasn't going to be able to hang on for another one. Her pussy was too active on my cock.

"Mommy?!"

"Yes, Augie," she moaned.

"Mommy! Something's coming."

"Let it come, Augie. Momma feels it too."

I abused her breasts with my hands & mouth a bit more and then grabbed her hips and started helping her work our sexes against one another.

Her hands went to her breasts - taking over after mine left - as I fucked the MILF onto my cock - holding out for her climax to begin.

I thrusted my hips up to meet her body as I pulled her onto me - then back apart again - and then together once more.