Dude, You Slept With My Mom

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(Bucket-List Progress: Week 30 - 71/104 = 68.27%)

(Bucket-List Progress: Week 30 - 71/104 = 68.27%)

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~~~ Week 30 - Saturday ~~~

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I've never been claustrophobic - but waking up with one body lying on top of you and two more pressed against your sides can be a bit much at certain times. This was not one of those times.

Overnight, my penis had softened and had slipped out of my sister's pussy - but she was still lying, very comfortably, on top of me. She was also still completely naked. She was starting to stir and I didn't want to wake her yet. I wanted to just enjoy the closeness.

The last few days with her had been such a major shift in our relationship - almost a role-reversal. I was no longer the needy little brother - holding onto my sister's back pocket and following her around everywhere she went. Instead, she had opened herself up to me. She had given herself to me so thoroughly that it felt like I was now the one in charge. She came to me when she needed me - and not the other way around.

In a small way, I thought I might miss her being the one that I went to. On the flipside, however, I no longer had to follow her rules. Rolling her onto her back in her bed the other morning and fucking the hell out of her had felt empowering - and somehow even more intimate than my special moments with Emily or April. That visceral - almost feral - lovemaking session with my older sibling had also felt so completely right.

I realized that Elise's eyes were open. She was watching me. I cupped her jaw in my hand and pulled her lips to mine. We just kissed - tenderly - again and again.

"You belong to me," I whispered.

"I don't *belong* to anyone," she argued, scowling at me.

Her body, however, gave lie to her words. She shuddered when I repeated them.

"You belong to me," I said again. "You're my sexy fuck-toy. I heard what you told Jessie, you know?"

Elise blushed and looked away. I pulled her face back towards mine and looked into her eyes.

"I am just as addicted to you as you are to me," I whispered.

"I'm mad at myself for being so... powerless," Elise said quietly. "I swear my fucking ovaries ache whenever I think about you. Hearing these women go on and on has my body wanting to be bred by you."

I squeezed her and kissed her.

"I would love that," I said, "but we're waiting. I'm not ready to share your body with some brat just yet."

Elise gave a nervous giggle. I hugged her again and gave her bare ass a squeeze.

"I want to wake Maggie up the way that I did you the other day...," I told my sister. "I'm going to pound her into the bed and fill her up. You want to come along?"

"Let Maggie have her special time," Elise said. "I'll stay with your two fiancées and snuggle. Maybe I'll even get a little more sleep - now that my irritating little brother isn't bugging me."

She gave me a wry grin. I kissed her and then rolled out from under her. I tried to avoid waking the other two - but they were already stirring. When I got to the bedroom door, I looked back to see the three of them grinning at each other. It looked like they were plotting some evil scheme. I shook my head at them and headed, naked, towards Maggie's room.

As soon as I got there, I slipped under the covers and then eased on top of her, pushing her knees apart. She opened her eyes and looked at me.

"Just what do you think you're doing?" she asked, giving me a sleepy grin.

I ignored her question, took hold of my cock, and rubbed the head of my dick up and down her slit until she moaned and opened herself to me. I rubbed the tip around her clitoris and then dragged it down her furrow until I reached the gateway to paradise. She was just opening the gates for me when I hurriedly shoved my way inside of her.

"You bastard...," she playfully accused. "Maybe I wanted to sleep in..."

I reached for her ass, gripped it in both of my hands, and then rolled to my back - pulling her on top of me. I squeezed her butt as I pulled her body down against mine.

"I have to do all of the work?!" she complained. "You really *are* a fucking bastard..."

Her lips found mine. I moved a hand from her ass to her swinging breasts and fondled them while still squeezing her ass as she began to ride me. The room filled with the sounds of our moans.

It took her only a minute or two to cum the first time. When I snickered at her for cumming so quickly after trying to argue that she hadn't wanted me to wake her with sex, she snarled at me and then sped up - hurrying towards her next release.

"Did you enjoy the sexy show in the hot tub last night?" I asked her.

"I did," she said. "I didn't want Brian to feel uncomfortable so I didn't join in."

"I figured that was the case," I replied. "That's why I thought you deserved a reward this morning..."

"If you're rewarding me then why am I doing all of the work?" she asked with a grin.

She gasped when I flipped her onto her back, hooked my arms under her knees, bent her in half, and started pounding my cock into her.

"Yes, my handsome stud...," Maggie crowed. "Pound my pussy and remind it who it belongs to."

Maggie's fingers dug into my biceps harder and harder as I brought her closer and closer to her release. I could tell it was going to be a good one. I whispered to her that she was making my balls boil and that I was going to fill her so full when she came.

My teasing words made her shudder and soon she was gasping and cursing and shaking as she climaxed. As I promised, I came long and hard in her - filling her almost to overflowing.

After we got done, I carried her to the shower and we got cleaned up. We had just gotten to the kitchen when the other three emerged - fresh from the shower as well. The rosy glow on their cheeks told me that the three of them had been up to a little hanky-panky while getting cleaned up. Elise squeaked when I pinched her ass and told her that she was cheating on me with my girls. The other two just laughed.

We all worked together to make breakfast and - as usual - fixed way too much. When we were done eating, we packed up the leftovers to heat back up before church the next day.

We had just settled into comfortable seats in the front room when Brian and Alyssa came in the front door. Alyssa looked even more radiant than usual. I was still trying to figure out why she seemed to be glowing when my sister teased her about getting sex for breakfast. When the former prostitute immediately shot me a guilty look, I realized that Elise had hit the nail on the head.

I was just trying to get my emotions under control when Jessie called my phone.

"Hello?" I answered.

"Sam has a question to ask you," Jessie informed me.

I listened as the young MILF held the phone to her daughter's head and told her to talk.

"Sam?"

"Yes?" I asked in reply, unable to keep from grinning.

"Can... Can I come visit?" she asked. "I miss seeing you."

I consider myself to be a pretty tough guy but - in that moment - I came close to tears.

"What's wrong?" Emily asked.

"Samantha wants to come visit," I whispered.

The room around me devolved into plotting and planning.

"Yes, you can come," I told the girl. "Bring Mommy with you."

She let go with an adorable giggle.

"I can't drive, silly," she said. "Mommy has to bring me."

"Oh...! Right," I replied. "Okay, that works. See you soon."

"I love you, Sam," she said.

"Don't hang...!" Jessie yelled - just before the line went dead.

I was still struggling with keeping my face from showing how messed up I was inside when Jessie called back. I handed the phone to Maggie - who was sitting beside me.

"Hello, Jessie," Maggie said with a smile. "Yes, Sam's here. He's trying to pretend that your daughter saying 'I love you' didn't turn him into a quivering bowl of Jell-O. Yes... You're welcome to come over. I think the girls are already planning out your visit. See you two soon!"

She handed back my phone and leaned over to kiss me on the temple.

"It's a good thing Jessie's not seeing your face right now or she'd be dragging you off to the bedroom to make another one."

"Probably...," I agreed.

"Go get dressed for an outing," Maggie said.

Everyone else was heading to change their clothes as well - so I followed them - leaving Brian and Alyssa in the front room with Brian's mother. They moved to sit on the couch beside her, where I had just been seated.

As soon as I returned, Maggie sent me to the garage - to put Samantha's car seat back in the SUV. I arrived back in the house just as Jessie and Samantha came in the front door. Samantha ran straight for me with her arms spread wide. I scooped her up, spun her around, and then hugged her. She pressed her lips to mine.

"Hey!" I objected. "No kisses!"

She giggled adorably and I couldn't resist digging my fingers into her ribs. She squirmed and squealed and begged me to stop. I looked up to see her mother watching the two of us. As soon as Jessie's eyes found mine, I could almost physically feel the lust that was coming off of her.

The spell was broken when Maggie stepped between us - breaking our line-of-sight. As I listened, she and Elise explained the plan that the girls had hatched.

Elise, Alyssa, Emily, and April would be taking Jessie off for some "kid-free" self-care time. They were all heading to get manicures, pedicures, facials, and whatever else a "spa day" entails. Meanwhile, Maggie, Brian, and I were going to take Little Miss Sunshine on an adventure of her own.

Samantha immediately wanted to know what kind of adventure. I could see that her mother was curious as well. Maggie, however, refused to spill any details - and the girls were already hustling Jessie back out of the front door so that they could whisk her off to the spa.

Maggie grabbed her keys while I went to put Samantha in her seat. Brian was waiting by the car when his mother came out - curious to see where he would be sitting. Both of us went wide-eyed when Maggie ordered us into the very back.

We climbed through the second row and squished ourselves into the tiny third row - which really wasn't made for two grown men to sit in together. I kept having to remember to pull my knees back together so that I wasn't touching him. He was working to do the same.

When we pulled up in front of my mother's house and Mom and Lena came down the sidewalk, I realized why we'd been stuck in the back. Lena tried to sit in the row with Samantha - right in front of me - but Mom made her take shotgun. Mom slid into the seat, closed the door, and then turned to give my knee a squeeze.

"Sam's mom!" Samantha squealed.

"Hello, cutie," Mom replied. "Where are we going?"

"I don't know!" Samantha bemoaned. "Maggie won't tell me..."

"A surprise?!" Mom gasped. "How exciting!"

"I suppose...," Samantha said, still working the sympathy angle.

Mom grinned and gave her hand a squeeze.

"Maggie's good at surprises," Mom told the child. "I'll bet we're both going to love it."

"You don't know either?" Samantha asked.

"Nope. She wouldn't say," Mom confessed. "She just told me to wear long pants. Maybe we're going exploring in the woods..."

"That doesn't sound like fun," Samantha replied a little sullenly.

"Really?" Mom asked. "Sam used to love exploring in the woods."

"Did you?" she asked, turning to look at me.

I nodded and said, "I pretended like I was in a fairy tale."

"I suppose *that* could be fun...," the little brown-eyed girl said, still grumping.

Samantha was just beginning to complain about how long the ride was taking when we pulled up to the stables.

"Horsies?!" she exclaimed.

"It certainly looks that way," Mom agreed.

When Maggie pulled into a parking space and parked the car, Samantha was quivering with excitement. Mom unfastened Samantha's straps. Maggie got her door open and started getting her out of the seat.

Brian and I were still trying to climb out of the car when the brown-haired urchin cut loose with a squeal of excitement that I was fairly certain that they could probably hear clear back at Maggie's house - miles away.

I came around the car to find a woman my mother's age leading a pony up to the three women and one small girl. The small horse was the color of spun gold. Samantha was pulling at Maggie's hand, trying to escape - to get to the adorable pony that the woman was bringing over.

The woman had flaxen hair pulled back into a ponytail. She was wearing a green tank top that fit her wonderfully - revealing a firm, fit figure. She had on a pair of blue jeans that looked painted-onto her long legs and rounded ass. Her brown cowboy boots made her hips sway and her ass jiggle in a most delightful way when she walked.

"This is Mrs. Hollister," Maggie told Samantha. "These are her horses. You need to listen very carefully so that you don't scare them. They might hurt themselves or you if they get too excited."

Samantha immediately quieted. I had to work to keep from laughing. You could see the pent-up energy and excitement bleeding off of the child and you could tell that it took every amount of self-control for her not to simply explode.

"Sam, turn on your glasses," Maggie directed. "The girls wanted to watch."

I had just started the live-stream when the stable manager knelt in front of Samantha, introduced her to the pony, and then showed her how to hold her hand to give him a treat. Mrs. Hollister laid a sliver of apple in Samantha's hand and then placed her palm under Sam's to support it and to show her how to keep holding it open.

The pony was already excited about the treat. He seemed to have as much energy as Samantha. The woman let him grab for the snack and Samantha squealed and yanked her hand away. For a moment, I thought he had bitten her - but she was just reacting to his teeth and tongue tickling her palm - and the apple slice disappearing into his mouth.

Mrs. Hollister produced another slice of apple and Samantha gave him another treat. She squealed exactly the same way the second time - and then raced for me with her arms spread wide.

"Did you see?! Did you see?!" she asked excitedly.

"Yes," I told her, laughing.

"Would you like to sit on his back?" the woman asked her.

Samantha wriggled and shoved out of my arms and I nearly dropped her before she got down. Her little feet were already running before they even touched the ground. Maggie intercepted her and helped slow her down enough for the stable lady to instruct her on how to properly mount a horse - or a pony.

Once Samantha was on the thing's back, my mother started snapping pictures.

"Take my picture, Sam!" Samantha ordered. "I want to show Mommy."

Maggie explained that my glasses were special and that Mommy was seeing her. My phone buzzed with an incoming call. I put it on speakerphone. Jessie assured her daughter that she, Elise, Alyssa, Emily, and April were all watching.

"I love you, Mommy," Samantha cooed. "What are you doing?"

"I'm getting my fingernails painted," Jessie replied.

"Aw...," Samantha moaned.

"If you want, you can leave the pony and come get your nails painted too," Jessie offered.

"No!" Samantha said quickly. "The pony's mommy says I can ride for a little bit."

"Oh, okay," Jessie said. "Don't have too much fun without me!"

"Bye, Mommy!" Samantha called out.

The pony's "mommy" snickered.

We spent another few minutes with the pony and then went to look at the horses in the corral while Mrs. Hollister took the pony back to his pen.

When she returned, we all started getting geared up to go on a trail ride. My stomach began doing flip-flops. I had only ever been on a horse one time in my life. I'd been about eight years old. I'd gotten scared and had never gotten on one again.

Mom must have told Maggie my story because almost immediately Maggie began explaining to Mrs. Hollister that I was going to require special care. The horse lady gave me a sympathetic smile, patted my arm, and assured me that she'd take care of me.

I was beyond embarrassed but Brian pretended not to notice. He seemed to have the same horse skills that his mother did. I suspected that they had come here multiple times when he had been growing up. After my traumatic experience, Mom had never tried again. We also didn't have that many opportunities to go on family outings - so there was that reason that we hadn't returned here as well.

Once everybody had their safety equipment on, had been introduced to their mounts, and had climbed aboard, Mrs. Hollister helped me climb onto her personal horse.

As soon as I was situated, the horse-woman stepped onto the same wooden barrel that I had used to climb aboard and then she threw her leg up and over me and the horse, and dropped into place in front of me. There was no saddle. We were riding bareback. Mrs. Hollister reached back, grabbed my arms, and pulled them around her - placing my hands on her toned stomach.

"Scoot up," she ordered. "You can't hold on properly if you're not pressed up against me."

She didn't stop telling me to scoot closer until I was pressed tightly against her body. As soon as my dick was firmly mashed against her ass and my arms were tight around her frame, we started off. A spike of panic shot through me and I squeezed the woman even tighter. She snickered at me and then gave a lewd little moan that did more to make me relax than anything did.

"You must have one hell of a cock," she whispered to me. "I don't usually feel that much bulge when I've got a strapping young man seated behind me."

She wriggled her butt. I moaned. She snickered and pushed her butt back against me a little harder. I swear my cock was trying to burrow between the horse's back and her rounded rump - searching for her pussy. Based on how tight the rest of her body was, I wondered how snug her vagina would be.

By the time we got to the turn-around point, I was getting so turned on from Mrs. Hollister's ass grinding against my tented shorts that I really wasn't paying attention to the horse anymore. The longer we rode, the hornier I got.

I glanced at her hands to see if she had a wedding ring on. There was nothing there - not that a ring meant that much - but the lack of a ring suggested that she wasn't married. I wondered though - because Maggie kept calling her Mrs.

When we returned to the area near the parking lot, we dismounted. Maggie suggested that I help the horse lady return the mounts to their pens. Just before Mom, Lena, Maggie, Brian, and Samantha headed off to the little country store, Maggie stepped close to Mrs. Hollister and whispered something to her. The horse woman's head shot up. She locked eyes with me and then those eyes dropped to my crotch. My pants were still pretty tight from all of the stimulation she had given me.

Maggie headed off with the others and left me to help the woman with the horses. The woman cleared her throat and then locked eyes with me.

~~~ Week 30 - Kimberly Hollister (#072) ~~~

~~~ Week 30 - Kimberly Hollister (#072) ~~~

~~~ Classmate: Lily ~~~ Partner: Benjamin (divorced) ~~~

~~~ Classmate: Lily ~~~ Partner: Benjamin (divorced) ~~~

"Take their leads and follow me," Mrs. Hollister ordered.

I couldn't help but admire her taut ass in her tight blue jeans. Her hips swayed wonderfully as she moved and walked. My eyes were glued to her ass the whole way. We seemed to be headed to a different stable than where I thought she had gotten the horses from - but I didn't have time to ask her about it before she led me around the back and then opened a paddock that had clover growing in it.

The horses were excited when they saw where we were heading. I barely kept a hold on them before Mrs. Hollister stepped close - bumping her front to mine - before taking the reins and removing the halter from the next horse. She mashed her body to mine again when she took the last one from me.