Dude, You Slept With My Mom

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(Bucket-List Progress: Week 29 - 70/104 = 67.30%)

(Bucket-List Progress: Week 29 - 70/104 = 67.30%)

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~~~ Week 29 - Saturday ~~~

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Emily, April, and I woke up and got into the shower to prepare for our day. I was already looking forward to getting Jessie alone. Emily and April, of course, noticed that my penis was already anticipating a sneaky rendezvous. They caressed my shaft and balls but only gave me enough stimulation to drive me crazy - not enough to grant release. By the time we got dressed and headed out of the door, I had the worst case of blue balls that I'd experienced probably since I graduated from high school. Even in the truck, the two were relentless.

As usual, we met Brian and Alyssa at the nursery to grab the last few things that we would need in order to finish up the job at Joseph Cambridge's house. It didn't take those two long to realize that I was edging like crazy. They did nothing to discourage April and Emily's torturous teasing. In fact, Alyssa became the worst of the three with naughty touches that only served to make me even more uncomfortable.

I'd wanted to get nasty with Alyssa for so long and now that she knew I was trying to hold it all in until Jessie showed up, the former prostitute finally gave me the inappropriate touches that I'd been longing for. Brian eventually had mercy on me and intervened. He told her to stop. The next time she brushed her body against mine - eliciting a moan from me - he even went so far as to ask her if he needed to tie her up so that I could use her body to get some relief. Alyssa was so shocked at his words that she finally realized that she'd gotten so wrapped up in joining in with April and Emily's antics that she'd stepped completely out of bounds.

A minute later, when the other two were still tormenting me, he grabbed my elbow, guided me to Alyssa's truck - and then hollered back to tell her to ride with April and Emily. He opened the passenger door and pointed for me to get in. He headed around to drive.

He didn't hurry to the Cambridge place but he also didn't dawdle. By the time we got there, Jessie was pulling up. Brian got out, gave her a quick explanation about what had been going on, and told her to drive me to my apartment and not to come back until she'd gotten me to cum at least twice.

Jessie looked at my face as I staggered towards her. She smothered a giggle and grabbed my elbow to guide me to the car. Jessie had just pulled away from the curb when Emily, April, and Alyssa drove up to the job-site in the other truck. Since I didn't immediately get a phone call or a text, I assumed that Brian had interceded on my behalf.

As she drove, I told Jessie what Emily had said about being able to smell her arousal and wondering if she'd been avoiding touching herself in anticipation of us getting together again. Jessie's eyes were wide as I shared that information with her. She admitted that she had not masturbated all week because she wanted to get my cock inside of her again.

"Should we just start off in the shower?" I asked her. "So that we have less to clean up?"

"That's fine with me," she said, blushing slightly.

"Why are you blushing?" I asked.

"I can't believe how much you've changed my life, these last few days," she said. "Samantha's talking about you non-stop. She listens better already. She was so worn out when we got home last night that I pretty much just fed her, bathed her, and put her to bed. She was out like a light."

Jessie glanced at my crotch and then fixed her eyes back on the road again before continuing.

"I laid there in my bed - wanting to finger myself while remembering you and Samantha working side-by-side all afternoon - but I had promised myself that I'd wait. My panties were already a mess when I pulled up to the job-site this morning. They're even worse now."

Once we arrived, I hurried to get the backdoor unlocked. Jessie went into the house and she headed straight for the bathroom. She dropped her pants to the floor, stepped out of her panties, rinsed and then scrubbed them at the sink, and then asked where a fan was - so that she could hang them up to dry. I watched her gorgeously-tight bare butt wobble around the apartment with her pussy leaking down the inside of her thighs.

By the time she got to the shower, I was naked and had the water warmed up. She slipped her arms around me, mashed her body against mine, and pressed her lips to mine. We made out as the water cascaded over us. My cock rubbed against her body. She shoved it down, hopped on it like a witch on a broomstick, and wrapped herself around me. I held her butt in my hands. Jessie held onto my neck. I worked my hips forwards and backwards - sliding my shaft against the bottom of her vulva.

We were both cumming in less than a minute. My jism ricocheted off the underside of Jessie's taint and butt-cheeks and fell to the floor of the shower. Jessie's pussy gushed all over my penis. My entire length was coated because I was still slowly thrusting my prick back and forth between her thighs. Her warm slickness ran down the sides of my shaft and dripped onto my balls, thighs, legs, and feet.

We kept our bodies intertwined when we finished that first climax together. We kissed and cuddled and enjoyed the warmth of the spray. I slid my cock back and forth between her labia until we were both almost ready to cum again.

The water started to cool and we realized that we were out of time. We hadn't even touched the soap yet. We turned off the spray, got out, and toweled off.

Jessie kissed me, took me by the hand, and led me to the bed. She climbed onto the mattress, lay on her back in the middle of it, and then spread her legs - inviting me in.

"Make love to me, Sam," she said softly.

I climbed between her legs and ducked my head to taste her and make her cum with my tongue. She told me that she didn't want my mouth there - she wanted my cock - but I just had to watch her face as I got her off. She didn't last long. She screamed my name as she came for me.

I climbed her body. Her sweet nectar dripped from my mouth and left a trail up her willowy frame as I advanced. My face was a mess, but she kissed me like she hadn't had any kisses in months or even years. At the same time that she gave me needy kisses, Jessie reached between us to get my cock inside of her. We both moaned as it slid snugly into place like a key into a lock.

"Fuck me, Samuel Jackson Fowler...," she ordered. "I need to feel you filling me up when you cum."

Jessie's brown hair and brown eyes captivated me. Her body was exquisite and highly attractive to me. I loved her smile, her kisses, and seeing her with Samantha. Jessie fulfilled something very different in me than Emily, April, or even Maggie did. I felt like I'd been searching for her and just hadn't realized it.

I made gentle, sweet love to the gorgeous young MILF who had captivated me. I kept things under control and stopped to let her recover when she came for me again.

As Jessie recovered from her most recent climax, I warned her that Emily and April would be trying to get her alone (or together) very soon. She snarled like a panther, rolled me to my back, and started on the next round - bouncing and grinding on my still-stiff pole. I held Jessie's ass in my hands and helped her fuck a little harder and faster this time. By the time she climaxed again, I was close to cumming.

I rolled Jessie to her back and started pounding my cock into her - determined to make her scream my name again before I filled her up. Panting for breath, she told me that she wanted to be fucked like a dog. I pulled my cock out of her. Jessie rolled over, got her knees under her, and raised her ass for me. She buried her face in the pillows and ordered me not to stop fucking her until my balls were empty.

I dug my fingers into her perfectly-shaped and toned butt and I pounded my cock into her like a SWAT team battering ram on a crack-house door - hammering and hammering until something finally gave. Jessie shrieked and moaned and cussed and groaned as I tried my best to ruin her snug-fitting pussy. When I finally felt my balls getting ready to explode, I warned her that I was about to fill her with so much semen that it was just going to pour out of her.

Jessie whimpered and shuddered - and came for me again - just as I began releasing my load inside of her. My fingers ached from digging them into Jessie's butt. I was sure I was leaving bruises on her hips and ass - but I'd pushed back against my climax for so long that I was worried that I had forgotten how to cum. When it finally began, my entire body hurt as the spurts of jism rocketed from my prick and fired inside of Jessie's churning depths.

Both of our bodies trembled and shuddered as I emptied my balls into her and she came yet another time. When I finally stopped cumming, I collapsed on top of her and just laid there, panting for air.

Several minutes later, we got up, showered quickly, and then I found her a clean pair of Emily's panties to put on. We got dressed and headed to join the others at the job-site.

As soon as we arrived, Alyssa headed my way. She was standing by the car when I got out.

"I was out of line," Alyssa said. "I let the heat of the moment carry me away. I set boundaries for you months ago and then I broke several of those this morning. Do you forgive me?"

"Always," I said.

She put her arms around me, kissed my cheek, and then stepped back.

"I'm glad that Brian was there to be the voice of reason," Alyssa said. "I really am sorry. That was totally uncalled for."

She glanced at Jessie and then back to me.

"Are you two feeling better now?" Alyssa asked.

Jessie blushed and nodded.

"There aren't many secrets with our group," Alyssa warned Jessie. "When Sam and I first met, he wanted to get with me - still does - or at least he pretends to sometimes. I really only think of him as a brother. Today, like a nasty and immature little sister, I teased and tormented him mercilessly. Sam has been looking forward to getting you to himself - and we all kind of went overboard."

April and Emily walked up at that point.

"Sorry," April said, hugging me. "We got carried away."

"It's my fault," Emily said. "I refused to let it go and I egged the others on."

I was still feeling a little perturbed with the two of them.

"Two days with no sex," I said. "That's your penance."

"It should probably be longer," Emily said glumly. "I'll take it. You guys okay to work now?"

"I want to get this finished so that we can start moving our stuff...," April said. "I think two days is generous as well. Thanks, Sam. Sorry."

With that, we all turned and headed for our tasks.

Emily decided that she would move Jessie around between the members of our team. We were all kind of working on different tasks - trying to wrap things up for Mr. Cambridge's project. It gave each of us a chance to chat with her and to work side-by-side.

I have to admit that I got a little jealous that she was talking and working with the others - but listening to snippets of their conversations and looking up to see her smiling at me filled my whole chest with a warm glow that I was sure the others could see.

By the time we finished all of our tasks and Emily had called Ron to come do the final walkthrough, Jessie was heading off to watch April snap the last few pictures of our work.

As usual, the customer arrived about the same time as Mr. Reynolds. We went over each segment of the project and made sure that Mr. Cambridge was happy with what we had done. Brian, Alyssa, and I picked up stray tools, trash, and leftover supplies while the others did the wrap-up.

Soon enough, we were all gathering beside the three trucks. Mr. Reynolds glanced at Jessie's car and then looked at Emily.

"I suppose you're going to want another truck...," he said.

"Maggie already requisitioned it and you already signed-off," she said, giving him an impish grin.

"Of course I did...," he said, shaking his head in disbelief. "I guess I should just be happy that you're all on my side..."

He held his hand out to Jessie.

"I'm going to guess that you're joining Sam's little harem and I'm still going to be holding my monthly staff meetings by myself...?"

"Yes and yes," Emily said, leaning between them.

Ron sighed and released Jessie's hand.

"Any castoffs to send my way?" Ron asked me.

I glanced at Jessie and asked, "Is your sister single?"

"Technically, they are *separated*," Jessie answered.

I turned back to Ron.

"I'll see what I can do. Jersey is a little meatier than Jessie but I think she'd be right up your alley."

"I'll be right up her alley for sure," he said, grinning.

"I'll talk to Maggie," Emily interjected.

"I'd appreciate it," Ron said, his smile fading. "Been going through a bit of a dry spell..."

"TMI, boss," April chirped. "We'll get Maggie on the job for you though."

"Thanks," he said, nodding - before ogling her briefly.

He turned and headed for his truck.

"Let's hit the diner...," Emily suggested, as Ron pulled away.

We loaded up and headed for our favorite eatery.

We'd barely gotten in the door before Rhonda was hollering at the "new girl" to see if she'd decided on a regular meal. When Jessie hesitated, Rhonda told her that she'd just get her what she had the previous day. With that, she headed for the kitchen.

"How does she remember?" Jessie asked.

"First," Emily said. "Sam's mom is a waitress for one of her jobs - so he tips well."

"Secondly," April added. "We're in here like every freakin' day."

Jessie nodded and headed off to the restroom with the rest of the herd. Brian and I hit the men's room, washed our hands, and headed for our booth.

"You get any more folks on your team and you're gonna need to find a new place to sit," Rhonda teased. "Either that, or Mel's going to have to make the booth bigger."

When the girls arrived, April had Jessie take her usual spot - on my left. She sat with Alyssa and Brian. As Rhonda started setting down plates of food, things got a little cramped - but we made it work. We were all used to bumping into each other when we worked together anyway.

Soon enough, the food was gone. Rhonda took the plates and brought us drink refills.

"Ron...," April prompted Emily.

"Right," Emily replied, nodding.

I leaned back so that she could see Jessie.

"Ron's mostly harmless," Emily said.

"Unless you count those creepy looks he gives us," Alyssa murmured.

"Right," April agreed.

Emily ignored them and continued.

"When it was just Sam, Maggie, and Ron," Emily said, "they used to have monthly 'staff meetings' where Ron and Sam shared Maggie."

"Why?" April asked, looking at me.

I shrugged and said, "Maggie had been going through a dark time. She pretty much craved any attention that she could get."

"Dad treated Mom like she was worthless," Brian said, nodding. "Mom started believing what he told her because she couldn't find a decent, steady guy. As much as I'm not too fond of my former classmate banging my mother, Sam treats my Mom with respect. I dare say he loves her more than any other man ever has."

"I *do* care for your mother," I told him. "Sorry about the creepy part."

He shrugged and said, "Mom's happier than she has been in years. When you all came to the hospital and I watched you interacting, I didn't know how to take it. Day after day, I watched and listened. I saw Mom respond positively to a man for the first time in a long time - and I saw a guy I barely knew act like my mother was worth something. I'm not about to shit on her parade when she smiles more than she ever has before."

Jessie looked around between all of us. She turned to Alyssa.

"I see what you meant," Jessie told her. "That whole conversation... just now... that could be so uncomfortable but you guys... you guys..."

She dropped her face into her hands, shuddered once, and then looked up again. Her eyes were wet.

"I've watched all of you as you've interacted with Samantha," she said. "Today, I got to know each of you a little. I'm already in love with Emily and April and - of course - Sam..."

"... of course...," April said, grinning. "Sam's a big teddy bear..."

"... until somebody threatens you...," Alyssa said. "Sam didn't know me from Eve but - when some random guy started giving me shit - Sam put himself between me and the danger."

"Did that with my mom too," Emily said. "She'll never get over him, I don't think. It's weird as fuck, sometimes, seeing her bat her eyelashes at my fiancé - but then I think about Sam seeing the bruise that my dad gave my mom and I remember the look on Sam's face..."

Emily wriggled in her seat.

"It's a bad idea for me to be this wet - since I'm on a two-day suspension..."

"About that...," I told her.

"No," she said, stopping me. "I need some sort of punitive reminder."

"Just tonight then...," I countered.

"If my mother and I are both after your cock tomorrow at your mother's house, she's not going to be too happy with us...," Emily said, grinning impishly.

April snickered - and then looked at me.

"I'm going to be super-horny by tomorrow as well," she said. "I'm too used to being put to bed with a pussy that's still tingling from your mouth or your cock..."

"I know...," Emily said, sighing.

Jessie glanced from us to the other two.

Alyssa grinned and said, "You'll get used to us."

"I still can't believe that you're allowing me in so easily...," Jessie answered.

"About that...," Emily said. "Maggie started this. She is still *technically* queen bee - though she never really acts like it. Some of the Coffee Club members are highly-protective..."

"Coffee Club?" Jessie asked.

"The original twelve moms that Sam fucked," Emily explained. "When Sam made his off-the-cuff pronouncement that he wanted to fuck every one of his classmates' mothers, Maggie already had a group of them meeting at her house for coffee and cards."

Emily looked back and forth between Brian and me.

"Does she still meet with them?" Emily asked.

I shrugged and said, "I don't know... maybe she slips away from the office."

"No clue," Brian said. "I guess she could do Saturday mornings. We're rarely there..."

"Yeah, I suppose...," Emily said.

She turned her attention back to Jessie.

"We take care of Elena's yard on Friday mornings," Emily told her. "Elena lets us use one of her cars so that Sam doesn't have to take the landscaping truck to his rendezvous. Sue does our retirement and investments. Maria handles legal matters. My mom was part of that group as well. I assume she still is."

April cleared her throat and said, "Emily's mother moved in with Sam's when Emily's mother finally filed for divorce and needed a place to stay."

"It was more complicated than that - but that's close enough," Emily said, nodding. "We'll see them all tomorrow at church - and go to Sam's mother's house after we go out to eat. We usually hang around there until dinner. She usually tries to convince him to grill out."

"Samantha is very much looking forward to meeting Sam's mom," Jessie said. "My mother was already asking what time she was supposed to show up - and where. I told her that Samantha was getting the cart ahead of the horse a little... Mom's a little excited that I've found 'a man'. I'm not quite sure how I'm going to explain all of this to her..."

Brian chuckled and said, "Just do like the rest of us - drag your mother in and let Sam and them figure it out."

"Mom's not that keen on my relationships...," I remarked.

"Yeah, well," Brian said, laughing, "see if you can keep from sticking your dick into this one..."

"He's already dicking Jessie...," April said quietly.