Dude, You Slept With My Mom?! Ch. 06

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Most people have a bucket list; I have a Fuck It list.
11.7k words
4.8
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Part 6 of the 8 part series

Updated 04/27/2024
Created 08/13/2023
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Note: Given how the relationship between Sam and Lena is developing, I've decided to change the category for this series from "Mature" to "Incest/Taboo". I hope that you'll stick with me. The focus will still remain on a veritable parade of MILFs - but, obviously, Emily's mom has a more unique relationship with our boy.

~~~~~

Week 12

(Bucket-List Progress: 19/104 = 18.3%)

~~~~~

The next morning, Emily and I started on the last portion of the landscaping project for Mrs. Ramirez - Lena's attorney and former schoolmate.

Midway through the morning, I helped the lawyer move her bed again. She bent over the right side of it, pressed her face onto the mattress, and I fucked her doggie-style. She came twice before ordering me to fill her with my seed. I did. After that, I rolled her onto her back and kissed her as I stroked in and out of her slowly. Once she came again, I got dressed and went to help Emily finish the yardwork.

On the way to lunch in the truck, Emily fished my cock out of my pants and sucked Maria's half-dried goo from my penis. I tried to get her to let me at least finger her, but she said she was waiting until the evening's session to get off.

As we pulled into the diner, she informed me that it had been more than a week since I had fingered Maggie in her son's bedroom - and that she was sure that my lover needed some quality time with me.

We ate lunch and went back to Maria's to finish up our work. Since we were done a little early, we loaded our tools and supplies into the truck and hurried back to the office. We checked the cameras - to be sure nobody was out front - opened the door, and slipped out to the front-office to talk to Maggie.

When Emily told her what she'd told me, Maggie got misty-eyed and stood to give her a hug. Emily shoved the two of us down the hall and said she'd babysit the phones. Maggie objected that I had an evening session and Emily told her that she could still ride my face to get herself a tide-me-over until we could schedule some real quality time.

Maggie finally agreed and we moved into the apartment and closed the door. I told my lover that I needed a quick shower and she said we could kill two birds with one stone. We undressed and she helped me scrub myself clean. She didn't touch my cock.

I dropped to my knees, reached between her thighs to cup her ass in my palms, and greedily sucked, licked, and nibbled her goodies. She leaned against the wall of the shower and dug her fingers into my scalp as I worked to take her breath away.

I gave her two orgasms before I let her go. She lifted me to my feet and kissed & hugged me. My stiff prick bumped against her navel. She cautioned me to go easy because I was going to have a busy night but I told her that she already had me aching with need. She giggled and pushed me away. We got dried off and dressed. We went back out front to relieve Emily so she could go shower.

Maggie and I chatted for a bit and then it was time for her to head to her house - to the "Den of Iniquity" - to get things ready for my next "appointment".

~~~

When I slipped inside of the back door, Maggie was holding the ski-mask - as well as the Donatello mask. She handed me the TMNT (Teenage Mutant Ninja Turtles) mask first. Once I had it on, she gave me the ski-mask.

"Another roleplay?"

"Kind of," she said, grinning.

"What do you mean, kind of?" I asked.

"You'll see ..." she said, grinning even more broadly.

I slipped the mask on and opened the door. No one was visible so I stepped into the room. The door was quickly pushed shut and I turned to my left to find two police officers standing one step away.

"That's him," the redhead said. "Just like she described him."

"Assume the position," the brunette ordered.

She grabbed my elbow and physically moved me three steps forward - to stand next to the bed. She put her right leg in front of my left, reached back to grab my shoulder blade, and bent me over. I threw my hands out, onto the mattress, to keep myself from tumbling onto my face. My heart was racing!

~~~ Week 12 - Liam Bailey (#20) ~~~

~~~ Mom: Carly (redhead), Dad: Jonathan ~~~

~~~ Week 12 - Daniel King (#21) ~~~

~~~ Mom: Elizabeth (brunette), Dad: Stephen ~~~

My mind was imploding. This HAD to be a session. Out in the hall, Maggie had just grinned at me.

The radio on one of the officer's shoulders squawked and I heard the dispatcher's voice call out. The police officer reached up and turned down the volume. This was NOT roleplay; these were real police officers. The ease with which the brunette had bodily moved me to the bed and bent me over it told me that she did this all the time. She was operating on muscle memory.

The two of them were standing on either side of me. The brunette remained on my left; the redhead had moved to my right. Each of them had a hand on my lower ribs. I couldn't have hoped to move even if I had thought I could escape. I was pinned between them. Their hips were close enough to mine that I swore I could feel their body heat through my jeans.

I could see a pair of handcuffs hanging from the leather loop on the brunette's pants - next to her handgun. Their shoes were standard-issue - glossy, black. Everything about them was 100% legit.

"Do you have any weapons on you?" the redhead asked.

I shook my head, no.

"Check him," the brunette ordered.

The redhead stepped behind me, bumped her crotch up against my ass, and started searching me. Her hands began at my collar. She used both hands, simultaneously, and checked my shoulders, my sleeves, my armpits, my ribs, my back, my chest ... When her hands moved down, sliding across my abdomen, my brain told my body that her hands would soon be touching me lower - someplace private. Despite the fact that I couldn't focus on any one clear thought, my body began to react to the images of where her practiced hands would be touching, searching, squeezing, tugging ... She stopped when she got to my belt.

She dropped to a crouch on the floor. I looked down to see her face between my calves. Her muscled hands moved up from my left ankle, searching, until she got to my knee. She switched legs. Again, her powerful fingers worked my body, from my ankle to my knee. She went back to the left, wrapping her hands around my leg, where she had previously stopped.

As her questing fingers moved up my thigh, I stifled a moan. I coughed as her hands brushed over my body where my leg joined my ass. She moved back to my right knee and searched upward. Closer and closer her fingers got to my growing manhood. I gasped when she touched it. She reached her left hand between my legs, grasped my rod, and ran her palm and fingers up and down it, measuring its length.

"Got something!" the officer announced to the other.

She stood to her feet, her arm still between my thighs, brushing against my ball-sack. She started stroking my cock through the cloth of my pants as her right hand searched my ass and my groin.

"Got a fucking club down his pant leg," she growled to her partner.

"Strip him," the brunette ordered.

She stepped sideways, to face me, giving her partner more room to work. I was still completely under their control.

The redhead reached around my waist to grasp my fly. She growled, "Don't move."

"Scoot your feet closer together," the brunette ordered.

My pants went to my ankles. The redhead crouched down, ran her hand up the leg of my boxer-briefs, gripped my penis, and began slowly milking me.

"The boy's fucking packing, Liz!" she told her partner.

"Do you have a permit for that firearm, young man?" the brunette asked me - as the redhead stroked my cock.

In seconds, the ski-mask was ripped off and I was lying on my face, on the mattress, with my wrists handcuffed behind my back. It had all happened in seconds. My shoes came off and bounced off of the wall by the door, my pants quickly followed. Once my underwear came off, they both knelt on the floor beside me.

"God, Carly! Have you ever seen one this big before?"

"Only on the computer," her partner replied.

They took turns, stroking my cock. On the downward thrust, they squeezed - milking me - and then used their fingers to abuse the head of my prick. I couldn't stop moaning.

"Think it'll fit?" the redhead asked.

"Maybe my ass," the brunette replied. "I don't think I could take it with my mouth or my pussy."

"Can we try?" the redhead asked.

The cuffs came off, they stood me up, and my shirt disappeared.

"Hands behind your head," the brunette ordered, "lace your fingers together."

I did as ordered. The cuffs snapped back into place. The redhead pulled back the covers on the bed and the brunette spun me around and sat me down. The two of them leered at me as they undressed.

They carefully removed the various pieces of their equipment and their uniform, making two separate organized stacks on the armchair.

The redhead had a lacey green panty-set on; the brunette was wearing black. It was edged in simple lace as well. The redhead was athletic with generous breasts; the brunette was a body-builder. No matter how buff I'd become with my job, I knew in a heartbeat that she could rip off my arm and use it to beat me to death - and probably not raise a sweat.

My stomach was still churning from the sight of her impressive physique when I felt the heat of the redhead's mouth surround my cock. It took her a couple tries but she eventually got it part of the way down her esophagus as well, before pulling off.

The brunette took her place. She couldn't get it to squeeze into her throat without gagging. After giving up on the deep-throat attempt, she was nice enough to suck me a bit - which brought me back to hardness after being intimidated by her powerful body.

The redhead moved a pillow down and the brunette moved onto the bed. Together, the two of them lifted me up and moved my body until my head was on the pillow and I was lying, stretched-out, on the bed.

The redhead's slit was crowned with a thin red landing-strip. She pressed my cock against my abdomen and slid her vulva up and down my prick, stimulating herself to see if she could take me.

The brunette approached my face and I worried about what she was up to. She nibbled and sucked my neck until I was moaning and then started making out with me. She was a talented kisser and I soon forgot about how scary her body was.

She stood up on her knees, leaned over to the redhead and gave her a lusty kiss. Then she straddled my face and I lost sight of what the two officers were doing. The body-builder's iron-hard thighs trapped my face. Her pussy was silky and slick. My mind soon slipped away from any concerns other than devouring her tender goodies.

I could feel the redhead lifting my prick from my stomach and starting to wedge it into her vaginal entrance. I quickly chucked my climax into Pandora's Box, grabbed the lid, and held on for dear life.

I was instantly lost in the euphoria of two women using my body to give themselves pleasure. Even as careful as I was being, the sounds they were making - and the stimulation they were generating - was causing me a large amount of stress.

Their toned, muscular bodies translated into toned, muscular pussies. One was working on my face and jaw - and one was gripping my cock like a pair of fists. It felt like I was moaning non-stop.

The sounds they made were the most feminine thing they'd done since I stepped into the room. These were no longer dominant women who controlled me. Well, I mean, I WAS still handcuffed ... but this was sex ... sex with two beautiful women ... two beautiful women who seemed very intent on using my body to cum. I was VERY okay with that.

I'd given the brunette one small climax by the time I felt the redhead's cunt clench along my length and she squirted her jizz on me.

The brunette climbed off, moved her head to where the two of us were joined, and cleaned up the slick mess with her tongue.

"You taste good, Carls," the body-builder cooed to her partner. "Switch me."

The redhead climbed off, and moved up to make out with me for a bit as the brunette settled her muscled-vagina down onto my cock. She got most of it in before we bottomed out. Her muscled thighs rippled as they moved against my own. My cock caused her six-pack abs to bulge a little.

"God, he's huge," she moaned.

"Ride him 'til you cum then let's un-cuff him," the redhead told her. "I want to see what he can do with that thing."

"He didn't cum in you?" the brunette asked.

"Nope."

"Shit!"

The redhead lay beside me and cuddled and kissed me as her partner rode my cock.

"I thought you were switching?" I asked her, when she paused.

"I won't make you lick your pre-cum from my snatch," she told me.

"He's got a talented tongue, Carls," the brunette told her. "You're missing out."

"Maybe next time," she said, winking at me.

I smiled for the first time since entering the room. The redhead climbed off of the bed, returned with the keys, and removed the cuffs.

"Thanks," I told her.

"Roll her over and fuck her," she whispered, before crawling back off of the bed with the cuffs and the keys.

"Carly!" the brunette warned.

I lifted and twisted. The brunette helped or I probably wouldn't have been able to manage it. She was a solid mass of muscles. Her head ended up on the pillow.

"Fast or slow?" I asked, sliding my cock in and out of her.

"As fast and hard as you can go, little man," she said. "See if you can make momma cum."

"Challenge accepted," I growled.

The redhead laughed and plopped down on the mattress beside her partner to watch me. After a couple minutes of me fucking the brunette, the redhead grabbed a pillow and handed it to me.

"She likes her G-spot bruised. Either flip her over or shove this under her hips."

I scooted forward (pushing her hips up), shoved the pillow under her ass, and went back to work. I sped up a little and did my best to bang the head of my cock against the front of her vagina each time I plowed into her.

"Fuck, yes!" the brunette moaned.

The redhead leaned over her partner's sexy form and sucked her nipples and areolas hard. Soon the woman's body was trembling and her channel was getting tighter. I started thrusting a little faster and harder - banging her G-spot and then her cervix with each stroke.

"Oh, fuck, yes!" she growled.

Still sucking one of her nipples, the redhead reached over and strummed the woman's clit.

"You've held off long enough," she told me, "cum with her."

Still ramming my meat-prod into the brunette, I raised an eyebrow at the redhead, asking for confirmation. She nodded.

I released the lid on Pandora's Box and plowed into the brunette. I gritted my teeth, holding off a moment longer, as her climax overtook her. When I couldn't take it anymore, I roared as I began pumping rope after rope of semen into the powerful woman's gripping vagina.

"Yessss," she moaned, wrapping her thighs and arms around me to pull me in even tighter.

She was still holding me when we finished cumming. I couldn't escape. I looked at the redhead and whispered, "Help?"

She laughed and leaned over to give me a lusty kiss.

I heard the door and turned my head to see Maggie stepping into the room. I growled at her. She just laughed.

"I need to ask you officers something," Maggie said.

"Shoot," the brunette said, still holding my body tightly to hers.

"I recorded all of that so I can watch it again later. Is that okay?"

"Only if you give us each a copy," the redhead said, laughing.

The brunette nodded to Maggie and then wrapped her arms around my neck and kissed the life out of me.

When she let me breathe again, I looked at Maggie and said, "You know you scared the shit out of me, right?"

"That's why I recorded it," she told me. "I'm sure Emily will get a kick out of watching it later."

"Who's Emily?" the redhead asked.

"His girlfriend," Maggie told her.

"Kinky," the brunette said, grinning.

Each of the officers got another kiss and then they finally let me escape.

I gave Maggie a kiss and a hug before I slipped into the hallway to get dressed. I left the three of them to chat and headed home.

I told Emily that she was going to have a hard time separating the tastes of the two pussies. She French kissed me to get the brunette's flavor and then sucked my dick. Using a little creative subtraction, she thought she had a good idea of what the redhead tasted like.

She laughed when I told her that Maggie had recorded it. Before we turned out the light, she texted Maggie to tell her that she was looking forward to watching the video.

~~~

I looked at the address twice - the Presbyterian Church. Melissa Jean Anderson - the reluctant woman who had turned into a wildcat before our session was concluded.

I parked the truck and walked up to the door. It opened as Emily and I approached. Mrs. Anderson smiled at us.

"Is Reverend Anderson available?" I asked.

"If this is about the landscaping job, you'll be dealing with me," she replied. "Is that okay?"

"That's fine," I said, smiling somewhat nervously.

"Your services come highly recommended by a very good friend of mine, Delilah Sampson," she said.

"I'm glad to hear that she was pleased enough with our work to recommend us," I said.

Mrs. Anderson looked me up and down like she was getting ready to devour me.

"Have we met before?" she asked.

"I don't know," I lied. "I'm Sam. I've been with RR Nursery and Landscape for a few years now. This is Emily, she's only been with us for a few months."

Mrs. Anderson extended her hand to Emily, shook it, and then to me to do the same.

"It's all good," she said. "I just thought you looked familiar."

"Do you have time, now, to walk us around and show us what you would like done?" I asked.

"Yes," she said. "Let me just grab a jacket and my notes."

She disappeared from the doorway for a moment - but left it ajar. I glanced at Emily who smiled, knowingly, at me and shrugged. I could tell that she thought it was funny that the woman was putting on an act about thinking she recognized me.

We had already decided that Emily was better at writing stuff down accurately than I was. She would prompt me with questions to ask to get extra details but - otherwise - she scribbled quickly. She was also a dab hand a doing quick little sketches to show customers what she'd gotten from their descriptions. I usually just took pictures of the property and showed the clients pictures of trees, shrubs, and flowers that were options for the sections or areas that they were filling in or covering.

Over the next hour, we followed Mrs. Anderson around the parsonage and the church, collecting descriptions of everything that she wanted done. The whole area covered half of a city block. I warned her - multiple times - that Mr. Reynolds was going to need to do the estimate. I also told her that it would, undoubtedly, be expensive.

"I talked to Maggie," she said demurely. "She informed me that she could take care of handling the ... um ... incentives. She was confident that I wouldn't get a better deal from another company and that I would be happy with ALL of your services."

Emily jumped in and said, "If Maggie's talked to you, you can ignore him. He just wants to make sure you aren't disappointed when we're finished."

The minister's wife looked at her, pointedly, and said, "I've definitely been happy so far. VERY happy."

Emily smiled like an angel, and said, "That's good to hear. Sometimes I really have to get ON him pretty HARD to get 100% out of him."

"Really?" the woman asked, smirking, glancing at me before looking back at my girlfriend.