Dude, You Slept With My Mom

~~~~~

~~~~~

(Bucket-List Progress: Week 26 - 57/104 = 54.8%)

(Bucket-List Progress: Week 26 - 57/104 = 54.8%)

~~~~~

~~~~~

~

~~~ Week 26 - Friday ~~~

~

When my alarm went off, the four of us got up and headed into the shower. Other than a few kisses and a bit of grab-ass (mostly me teasing Maggie), we quickly got through our morning routine without any delays.

Maggie headed home. The rest of us headed to Elena Moretti's to get started on her yardwork.

When we arrived, Brian was in the truck with Alissa. He got out and walked over, smiling. Somehow - from the look on his face - I knew that he had watched my session with the pierced MILF. I looked from him to Alissa. She started laughing.

"I told you that he'd be able to tell," she informed him.

"You look like you're either dying to ask me something or dying to tell me...," I told Brian.

"Both," he said, nodding.

"Okay, shoot...," I replied.

"How bad was it? You made it look almost... normal. You were a little cringy on the butt stuff but got over it..."

I glanced at Alissa and then turned back to him.

"My motto is: There's no reason to fuck them in the ass when there's nothing wrong with their pussy."

He turned to Alissa. She started blushing - her eyes flitting to me before returning to him.

"I *have* done it. It was okay. I don't anticipate us..."

"Got it!" Alissa gasped, looking uncomfortable.

I couldn't help but laugh at her. She slugged me in the arm. It throbbed a little but I wasn't about to let her have the satisfaction of knowing she'd connected - though she probably knew.

Brian turned back to me.

"Okay, so... Alissa *tried* to dissuade me - but I was just too damned curious about how it would go. Knowing that they regularly watched you, I made her pull up the live-stream."

"And?" I asked.

"You... You put on a pretty good show," he said.

"Uh... Thanks?"

He laughed.

"I'm not gonna lie, I would never have done anything with that woman - but you definitely handle that shit better than I would. I've gotta tell you that - by the time you were done - we were both fidgeting. I had *not* anticipated getting uncomfortably horny while watching your little show - but Alissa and I turned it off and looked at each other and... well... Thanks, man."

Alissa's face was buried in her hands.

I heard two girls giggling from behind her. The former prostitute shrieked and jumped when one or both of them pinched her on the ass. She turned around and glared at them.

"Good job, Honeybunch," Emily said.

"I...," she began to rant.

She froze for a moment and then turned and headed for the shed that held the riding mower.

"Hey!" Emily yelled, heading after her.

April laughed and followed them.

"I don't know that I'll watch any more of your... uh... sessions," Brian said quietly, "but it made for a fun evening and - though this is still super-bizarre to me - I can see the appeal. You also definitely seem to have an approach that works. I've gotta admit that I'm tempted to tune in again."

"Just... uh... keep in mind," I said, "if you see me with one of your friend's mom's - it'll either be really awkward - or really hard to keep a lid on it."

"Noted," he replied, nodding.

He waved his hand around the yard.

"Alissa said there was a lot of shade here. I brought a lawn chair. I'm still not good on my feet for much more than a half-hour but I think I'm getting there."

"Just don't push yourself too much," I told him. "We have jobs lined up for weeks and weeks into the future. The sooner we get you to 100%, the sooner we can ramp things up."

"So... you all just spend Friday morning mowing some woman's yard...?" he asked, obviously curious about the use of our skills.

"Elena Moretti is a woman who is particular about her property - with the ability to afford our team to keep it looking good."

He nodded, looking pensive.

Out of the corner of my eye, I saw our benefactor coming out of the garage.

"Speaking of the goddess...," I whispered, turning towards her.

She smiled as she got closer. I glanced to the right to see the girls beginning to get to work. I didn't see anybody bleeding so I was hopeful that things had smoothed out.

"Good morning, Mrs. Moretti...," I said, offering a little bow.

She smirked at me, glanced at Brian, and then looked back.

"This is Maggie's son, Brian," I informed her. "He had a close call with a passing vehicle and is recovering. He's expressed interest in joining our team and came today to stretch his legs a bit and see what we do here. He and Alissa are getting to know each other little by little... They're both being cautious."

The professional woman gave Brian an appraising look.

"Sam and Maggie have assembled a quality team who have established themselves as - by most accounts - the premiere landscaping service in the city."

"I do admit to some trepidation at being able to keep up," Brian said, nodding.

Elena glanced at me and then looked back at Brian again.

"Listen to Sam and Emily and I have every confidence that they'll be able to turn you into a valuable addition. Alissa and April have been attentive and are both stellar. Their team has not even gotten to the Mayor's property yet and the man already knows each of their names. He's bribed at least two other clients in order to get moved up on the calendar that your mother maintains."

She turned to me.

She grinned and asked, "Are you letting the girls do all of the work today?"

I glanced their way for a moment and said, "They were... negotiating for positions and it looks like I've been left out of the bidding... You wouldn't happen to need your bike detailed or anything...?"

"Perhaps another time," she said, smiling. "I was heading out and saw a new face and thought I'd come introduce myself."

She turned to Brian.

"It was a pleasure to meet you," she said. "Please give your mother my regards."

"I will," he said, "and the pleasure was all mine."

He nodded his head to her. She nodded hers as well, turned, and headed off for the garage.

As usual, I watched her walk away - admiring her perfectly-shaped posterior - waiting for her to catch me. I noticed that Brian watched my eyes - and took in the view for a moment as well.

We had turned to watch the girls work, not saying anything, until Elena pulled out of the garage and drove off. Today, she was in the black Porsche.

"Nice ride," he commented.

"She owns at least one dealership," I informed him. "She's got a car sitting on the lot that I use for my sessions - so I don't have to drive the landscaping truck and advertise who I am."

"I wondered how you were driving that truck to those sessions," he said.

He glanced down the street.

"Goddess is right...," he said. "Damn!"

"Yeah..."

"You... She...?"

"Yeah..."

"How... was it?"

"Goddess."

He looked into my eyes for almost a full minute without speaking and then just nodded.

"If you ever live-stream...," he said.

I laughed and shook my head.

"Sorry, dude," I said. "She's in the Coffee Club. They all know who I am. I don't wear the glasses with them. Although, I screwed up with Susan Hall the other day... So maybe never say never..."

"I can hope...," he said.

"Just so you know," I told him. "I can almost cum on demand - and easily outlast even the most experienced woman - but she absolutely destroys me every single fucking time."

"How many times have...?"

"I... uh... five... maybe six?"

"Shit, dude!"

"Absolutely beyond description and - if the next 50 women that I fuck end up being petri dishes for communicable diseases - this whole fucking thing was worth it for just one time with her."

I glanced over to see Emily fighting with the weed whacker.

"I'd better get to work or she's gonna fire me. She must've really been pissed to take that on. They *always* leave that for me."

I pulled on my gloves and headed her way. By the time I got there, she was cussing and looking like she was about to break something.

"Go grab your water and make sure Brian's not overdoing it," I told her.

She took a lungful of air to yell at me and then just huffed and stomped off.

I checked the line. The spool was all fucked to hell. I sat down in the grass, pulled the trimmer apart, and started rewinding the trimmer line. I glanced over to see her watching me while Brian tried to talk to her. Once she saw that I was having trouble with the equipment as well, she deflated a little and started responding to him.

By the time I got the line fixed, got everything back together, and picked up where she had left off, she had calmed down and the two of them were visiting like old friends.

She caught me looking and motioned to me that she could take back over. I waved her off, telling her to stay with Brian. When I glanced again, she was taking him on a quick tour around the property. Soon enough, they were back to Alissa's truck and Emily was digging the lawn chair out for Brian to sit down. I finished what I was working on and waited for her as she walked back over.

"He alright?" I asked.

"I probably should have done the tour before he'd stood around for a half-hour," she said. "I think he's alright though. He's definitely stronger."

"Good. He tell you he watched the show."

"Yeah," she said. "He was surprised at how much he liked it. Most guys like porn, right?"

"I guess you'd call it porn...," I said hesitantly.

"It is most *definitely* porn, Fatdick," she said, laughing. "You get my motor running every time."

I bent down and kissed her. She kissed me back and groped my dick.

"You two see anything that I should be doing instead of trimming?" I asked her.

"Stick with what works," she replied, smirking.

I swatted her ass.

"I'm gonna go get the pole saw," she said. "There are a couple busted limbs that need to come down."

I nodded. She turned and headed off. She turned and caught me ogling her ass. She grinned and wiggled it a little more as she continued on.

Maggie was standing beside Brian's chair when I finished my work.

"He alright?" I asked her.

"Yeah," she replied. "He wants to go to the diner with you. As soon as we finish lunch I'm taking him home. He's pushing a little too hard."

"Mom...," he objected.

I shot him a look and he knocked it off. I caught movement to my left and noticed that three sweaty females were backing me up. He's eyes went from face to face. Nobody was on his side.

He sighed.

"You can ride to the diner with Alissa," she told him.

I offered him a hand up - out of the chair. He took it after a half-second of hesitation.

Alissa grabbed the chair, folded it up, and dropped it into the bed of the truck. She had the door open already by the time I got him there.

"Not an invalid...," he complained under his breath.

I left his not-quite-girlfriend to manage his attitude. I went to jump in with my crew. Maggie was already in her vehicle.

We drove to the diner, let Maggie and Brian use the bathroom first, and then sent them to our booth with instructions to flag the waitress down to get their orders in.

By the time we got out of the bathroom, they had drinks. As usual, ours were waiting on the table.

"We just ordered the same thing you guys get," he noted as we walked up.

Alissa glanced at me and smirked. April smiled as well. Both of them remembered the first time they'd come with us - and how they'd remarked about how big the meal was. Now, they mowed through it just as quickly as Emily and I did.

We visited for a few minutes and then the waitress and the owner came out - with him helping her carry the trays with our meals. I introduced the owner to Maggie and her son, explaining who they were. He greeted them and then headed back for the kitchen. The waitress asked if we needed anything else and then headed off to take care of her other customers.

Brian looked from his plate to the ones in front of Alissa and April. We laughed at him.

"Eat what you can," I told him. "Alissa will probably offer to help you finish it."

He just shook his head and picked up his fork.

The four of us that always ate this amount were done in our normal amount of time. The other two looked at us with wide eyes.

"How...?" Brian asked.

"Practice makes perfect...," I told him.

"I hate to ditch you guys," Emily said, "but we need to run to the nursery before we can head back to Avery's."

"Go...," Maggie said, waving us on with her fork.

Alissa cut a slice from Brian's pile of food, stuck it in her mouth, and then offered him a kiss. She had a little gravy on her lip and was grinning from ear to ear. He grinned back, leaned in, and kissed her.

She hopped up and chewed her food as we headed for the door. I met the waitress at the cash register, paid for the meals, and gave her the tip. I waved to the owner/cook and headed out behind the girls.

We hit the nursery, grabbed what we needed, and then hurried to the job-site.

The afternoon flew by. I reminded April to get some action-shots.

At quitting time, we gave Alissa kisses and headed for the truck.

"You've got a session tonight," Emily informed me immediately.

I'd barely gotten the driver's door closed. I was still reaching for the seatbelt.

"On Friday?" I complained.

"Yes, Mr. I'm Drowning in Pussy...," she teased. "You've got a nun who's having second thoughts about her vows. She reached out to your favorite pair of naughty preacher's wives and they've got a full evening planned for you..."

April laughed as she watched my face as I processed what my perverted pixie was telling me.

"What happened to all that muttering I heard a minute ago?" the blonde asked me.

I gave her a side-eye. She laughed louder.

It had been a while since I'd seen (or fucked) Delilah Sampson and Melissa Anderson. My mind, of course, flashed back to that first meeting with each.

Mrs. Delilah Sampson was the very first MILF I fucked after Maggie. She'd been tied to the bed. It was the first night I'd worn the mask to protect my identity. I smirked, thinking back to how many times the woman and I had fornicated together. The mask hadn't been too effective with the Coffee Club members. They were quickly recruited to be Maggie's assistants.

In fact, Mrs. Anderson - the second minister's wife to have an affair with me - had been brought into the fold, as it were, by Delilah Sampson.

Delilah tied the woman to the bed and then kept her from seeing me until she had accepted that she had been set up and that she was going to get sucked and fucked without giving implicit permission. Melissa Anderson - her friend had told her - was being cuckqueaned by her husband.

The Methodist minister spoke gently to her nervous friend about her husband's sins, telling her that she had nothing to be ashamed for for wanting to participate in sex acts with a willing male. I was the willing male that Delilah Sampson delivered to the friend that she had tied to the bed to keep her from running away.

Though not the most beautiful MILF I had fucked, it was easy to see that Melissa Anderson hadn't received amorous attention from a man in quite a while. The sex with her was just as raw and highly charged as it had been with Delilah Sampson. The level of emotional starvation the woman had been going through had me wanting to do everything within my power to do whatever I had to in order to help her in her time of need. I had cum just as hard as she had - just like I had with Delilah.

I could feel my cock growing - and my pants struggling to contain my expanding member. I suddenly realized that I was still just sitting there - as the two young women beside me watched me return to our present reality.

"Back again?" Emily asked, smirking.

April glanced down at my crotch and snickered.

"He's either super-excited about this nun... or replaying his adulterous affairs with those minister's wives," she told Emily, glancing over at her.

"Both, if I had to guess," Emily replied.

I pulled on my seatbelt, stuck the key in the ignition, and started the vehicle.

I don't remember most of the trip home - or the shower. April later told me that she had gone so far as to tease her fingertips across my ball-sack while I'd been cleaning up and I hadn't even responded. From what they said, Emily had finally told her to stop before she caused problems.

I numbly got dressed, ate whatever the girls had fixed, and headed to trade the truck for the Corolla. The address Emily gave me was farther than I usually had to travel - at the very edge of the city.

When I finally pulled up in front of the place, I found myself at a small Catholic church that looked like it belonged in a tiny town - not a bustling city. I checked the address again. It was right. There was a solitary light on inside - which kind of surprised me - so I got out and headed up the walk.

The door began to open when I got halfway up the path. Delilah Sampson stuck her head out and looked at me. I froze in my tracks. She was wearing a nun's habit - the classic black and white getup.

She snickered and waved me forward. When I got to the door, she stepped back so that I could enter. She closed it up as soon as I was inside.

Melissa Anderson was there as well - and dressed exactly the same as her partner. I looked back and forth between them.

"Oh...," Mrs. Anderson moaned. "I had not realized how I've missed you until this moment."

I gave her what I hoped was a winning smile and said, "I've missed you as well."

"I'll bet you've said that to half the women in the city by now," she replied, smirking, "but I appreciate your words."

I stepped into her personal space and her chest froze mid-breath. I leaned down until my lips were millimeters away from hers. I looked deeply into her eyes and then leaned forward just enough to allow our lips to meet. I didn't kiss her - I just held them there for five seconds - and then leaned back and stood back up - still looking into her eyes.

"Lord Jesus," she breathed, "forgive me for what I'm about to do - yet again."

Delilah Sampson snickered at her friend and stepped over to claim a kiss. I reached around her waist, cupped her ass in my hand, and pulled her more deeply into the kiss.

The whole kiss was extra erotic because of the outfit she was wearing - which was highlighted in my mind as I felt the texture of the cloth in my fist as I hefted her bulbous butt in my hand while returning her kiss. My cock was as hard as iron.

Mrs. Sampson gave a heavy sigh.

"We're here for someone else," she said, "but - if you happen to have anything left after you finish with Gabriela, Melissa and I have been looking forward to fornicating with you again...

"Fornicating...," Melissa said quietly.

"Can you think of a better word?" Delilah asked her. "It is vulgar - like our act of intentional sin - it's an announcement of our violation of our marriage vows - and it's so emotive of the physical act - the sound of two sweaty bodies slapping together as they become one - as their sexes wrestled and writhe against one another..."

Her friend gave a little whimper. Her two hands were squeezed into fists, pressed against her hips - like she was trying to keep from touching herself.

Her eyes zoomed in on mine. The need - physical, emotional,... even spiritual... was clearly evident.

"I'll take care of you," I promised.

"It... It won't... take long...," she stammered, her voice edging like I was sure that her body was.

I turned back to Delilah. She was holding a priest's robes and collar.

She gave me a wicked smile and crooked a finger at me. She moved from the foyer through the open doors to the small sanctuary. As old as the building looked on the outside, the interior was surprisingly clear of dust and clutter. She noticed my wandering eyes and explained.