Ms. Jackson Ch. 02

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Hailey's sisters come home for the holidays.
13.5k words
4.76
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Part 2 of the 3 part series

Updated 06/08/2023
Created 09/29/2016
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jeffincognito
jeffincognito
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Standing on my tippy toes I reached up and was just able to place the star on top of the tree.

"It looks perfect!" Hailey said with excitement.

I stepped off the stool and took a look at the newly decorated Christmas tree. Hailey gave me a kiss on the cheek and disappeared back into the closet in search for more Christmas decorations.

"Yeah, good work stud." Ms. Jackson said with a quiet voice, and then she slapped me on the butt. Hailey emerged from the closet only moments after, carrying a nativity scene.

This had become a little game that Ms. Jackson liked to play ever since we had given into our physical desires for one another a few months prior. Hailey still had no idea that I was fucking her Mom of course. That's what made the game fun for Ms. Jackson. Whenever she could get away with it she would tease me.

When Hailey wasn't looking Ms. Jackson would wink at me, or blow me a kiss. If Hailey ever left the room for a moment Ms. Jackson would plant a quick hard kiss on my mouth. Shoving her tongue down my throat and then retreating quickly before her daughter returned.

Once during dinner Ms. Jackson reached underneath the table, undid my fly and slid her hand into my pants. I nervously glanced across the table to Hailey, but she didn't seem to notice. Ms. Jackson's thin fingers curled around my half swollen shaft and pulled it out of my jeans. The room temperature air felt refreshing on my sensitive skin but I was not relaxed. I shifted my nervous glance from Hailey to her Mother. But Ms. Jackson did not look at me. Her attention above the table was focused on stabbing her buttered carrots with her fork and then eating them with delicate little bites. My half swollen dick quickly became fully erect in Mrs. Jackson's gentle grasp. Realizing that Ms. Jackson was not going to acknowledge me I scooted my chair forward, stomach against the table, making it easier for her to reach me, but also making it less likely that Hailey would notice anything unusual going on underneath the dinner table.

I felt Hailey's foot rub against mine. I looked up at her, she was smiling at me.

Oh great. I'd love to play footsies with you while your Mom is jacking me off. This is insane.

Very slowly and very carefully Ms. Jackson began stroking me underneath the table. I covered my whimper with a cough.

"Babe, are you okay?" Hailey asked me.

"Oh...yeah. Fine. Just choked on the broccoli." I said, taking a sip of water while Ms. Jackson continued to stroke me.

"So Hailey, how is practice? You are the lead right dear?" Ms. Jackson asked her daughter.

As Hailey began to tell us about memorizing lines for Kate in her theatre classes rendition of Taming of the Shrew, Ms. Jackson released my hard cock. Her hand appeared above the table and reached for the butter tray. With her knife she sliced off a slab of butter seemingly for her bread. Hailey was deep in her story at this point and probably wouldn't have noticed but, being cautious Ms. Jackson lowered her hands under the table again and instead of buttering her roll she placed the newly cut slab of butter onto her right palm. She placed the knife on the table and raised the dry roll to her lips. Meanwhile Hailey was discussing how the props are currently being made but are behind schedule. The play might have to be postponed until February.

Underneath the table Ms. Jackson placed her buttered hand on my throbbing shaft. She rubbed my twerking cock up and down, buttering it up like she had buttered the turkey for thanksgiving. The butter soon grew soft and melted from the friction, oozing between her smooth fingers and drizzling down my shaft. Her hand now slid easily up and down my buttered cock.

"Hummfff...humf" I choke on the broccoli again to cover my gasps. "Excuse me."

Hailey continued with her story, Ms. Jackson watched her daughter intently. Apparently enthralled with her daughter's narrative. Her hand pumping my cock as furiously as she could now without making it too obvious.

Oh my god I am going to bust!

I put my utensils down and grabbed my napkin, and as inconspicuously as I could, lowered it beneath the table. Somehow picking up on the cue Ms. Jackson focused her attention on my sensitive head. Wringing my cock in her hand while continuing to pump up and down. I prayed Hailey wouldn't notice the strained look on my face while I attempted to remain silent as I jizzed into my napkin underneath the table. Ms. Jackson slowed her pace but kept her pressure firm as I shot the remaining loads of cum into the dinner napkin. When finished, Ms. Jackson wiped her buttered and cum stained hand with her own napkin underneath the table. Then she continued eating like normal, as if nothing had happened, not once taking her eyes off her daughter to look at me.

"Hey Mom, look what I found." Hailey said, bringing me back to the present. They were huddled, looking at something. Ms. Jackson laughed.

"What is it?" I asked.

They parted and made room for me. In her hands Hailey held a small photo, framed with popsicle sticks, a string attached at the top in a loop so that it could be hung like an ornament from the tree. It was crinkled and looked a little dated. It was a family portrait with Santa Claus, minus Mr. Jackson.

Hailey couldn't have been older than twelve or so in the photo. She sat on Santa's lap, showing off a smile full of braces. This must have been her awkward phase. She was a cute little girl but this gave no hint to the beautiful young woman she would blossom into. A much younger Ms. Jackson stood to Santa's right. Her blonde hair was longer than it was now. She wore a thick sweater that did its best to hide her massive melons. She held a baby in her arms. Hailey's little sister, whom I had never met. She was currently away at boarding school. To the right of Santa stood two identical blonde girls that looked to be in their teens. They were even wearing matching outfits.

"These must be your older sisters?" I asked Hailey, pointing to the two girls.

"Yeah. Rachel and Leah." She answered.

"They used to dress alike." Ms. Jackson said, "But then one day they decided never to wear the same thing again. If one came upstairs wearing the same shirt as the other, one of them would have to change. I think it was part of them trying to find an identity outside of their sister. The school councilor told me that was a normal thing for identical twins to go through."

"I just can't believe how different you look Hailey." I said.

"Wait till you see my older sisters. They've changed even more."

"Rachel is the one that's married and had a baby in June, right?" I asked.

"Yeah. Her baby is so adorable. I can't wait to see him." Hailey said.

"What about Leah? Is she married?" I asked.

"Ha-ha, heavens no. I will be shocked if that one is ever tamed." Ms. Jackson laughed.

"You'll get to meet them tomorrow. They are staying here for the holidays." Hailey said.

"I look forward to it."

But I wasn't really looking forward to it. Three more people in the house, plus a baby, made it less likely that Ms. Jackson and I would find the time to perform our sinful ritual.

Xx

The winter air permeated my thin jacket. As my fingers untangled the mess of Christmas lights they were beginning to lose feeling in the cold. Hailey and her Mother were in the kitchen preparing dinner. I had been assigned the task of stringing lights along the roof. Ms. Jackson wanted everything to be perfect for the return of her oldest daughters.

The sound of tires crunching over freshly fallen snow stole my attention away from my current task. A blue Prius made its way down the quiet street and pulled into the driveway. For some reason I didn't picture Leah driving a Prius.

This must be Rachel and her family.

I made my way down the ladder. I could hear the sounds of car doors opening, followed by the sound of a crying baby. Reaching the ground, I turned to see a thin man struggling to lift a suitcase out of the trunk. A Woman leaned into the backseat, lifting her child out of the its car seat. She wore a fur hat, a wool scarf, heavy jacket, leather gloves with matching brown leather boots. All that could be seen was her face.

Wow. She looks so much like her Mother.

Her eyes were crystal blue. She also shared her Mothers high cheekbones and clearly defined jaw line. Her red lips were in sharp contrast against her porcelain skin.

"Hello. You must be Hailey's boyfriend." She said to me.

"Hey. I'm guessing you're Rachel?"

"Yes. This is our son, and that is Jacob, my husband." She said, gesturing to the man still struggling at the trunk. "It's good to finally meet you. I am excited to get to know you, but for now I'm going to get this little one inside. It's much too frigid out here."

"Yeah, of course. I'll see you inside." I told her. She rushed inside and I stepped to the rear of the car.

"Do you need some help?" I asked Jacob.

"If you don't mind."

I took hold of the suitcase he had been attempting to get out of the trunk and lifted it up with one arm. To be fair, it was pretty heavy. I reached in and grabbed another bag, leaving the smaller two suitcases for Jacob.

"Thanks. Really appreciate it." He said to me.

"No problem. How was the drive?"

We made awkward small talk as we carried the luggage to the front door. We entered and set the bags in the living room. Thankfully the sound of the Girls happy reunion gave us reason to end our forced conversation. Hailey was aweing over the baby while Ms. Jackson and Rachel laughed at an unknown story one of them had just finished. I left Jacob in the living room to put away the ladder.

I wasn't outside long when a cab pulled up to the curb. The back door opened and two furry boots emerged. Followed by a pair of thin legs.

This must be Leah.

"Damnit. Did Rachel beat me here?" she said, looking at the Prius.

She wore a beanie, blonde hair stuck out from underneath the edges. Dark sunglasses covered her eyes. Her trench coat stopped several inches above her knees, giving the appearance she wasn't wearing any bottoms.

At least I assume she is wearing bottoms.

"Mom!" she yelled as she walked past me towards the house. Ms. Jackson came to the front porch.

"Leah! My dear, welcome home." Ms. Jackson said.

"Do you have any money? I need to pay the cab driver." Leah asked. The cab driver had now unloaded her two suitcases onto the curb and was standing impatiently.

"I don't have any cash on me. Give me a few minutes to find my credit card." Ms. Jackson answered. The cab driver gave a dissatisfied grunt.

"It's okay. I have some." I offered, pulling the bills out of my pocket.

"Thank you so much. I'll pay you back." Ms. Jackson said. By the quick look she gave me I knew she wasn't referring to a monetary compensation.

I gave the driver his money while the girls, including Leah went inside. The cab pulled away, leaving me alone outside with Leah's suitcases.

I guess she assumes I'll bring her bags in.

Despite my annoyance I was still a gentleman. I took hold of her bags and lifted. The zipper on one of her bags must have been loose because when I lifted it the front flap fell open and dumped some of its contents onto the sidewalk, which was partly covered with a thin layer of snow. I quickly knelt down to retrieve the spilt items but couldn't believe my eyes.

What the hell? Is that a dildo?!

It was. It was a giant rubbery, flesh colored dildo with incredible detail. It even had little veins on the underside. Next to it lay a rubbery ring with two bulges on either end. I had never seen one of these before but I imagined it was meant for a penis. And next to that was a bottle of lubricant. I quickly grabbed all of them and shoved them back into the bag. I looked up to make sure no one had seen. The front door was shut; everyone was safely inside. I felt I could risk a quick peek into the open bag. It was full of sexual items! Lingerie, handcuffs, vibrators, etc. It seemed Leah had brought one bag entirely for her sex toys. I quickly zipped it back up and headed inside.

Inside I found Ms. Jackson, Hailey and the baby. It smelt like dinner was almost ready, and I was starving.

"Everyone's getting washed up for supper. Do you want to change your clothes really quick and then come back up?" Hailey asked. "And take Leah's bags downstairs, she's staying in the room across from us."

Oh lovely, maybe I'll be able to hear her use her "toys" during her visit.

I left Leah's bags outside the door to her room and went to mine. I hung up my jacket, kicked my shoes off and dropped my pants. Then I started pulling my shirt over my head. The door opened and someone entered.

"Hey Hailey, can I borrow...Whoops. Sorry, I thought you were my sister." Said a voice that sounded like Leah's.

By the time I had gotten my head out of my shirt she was gone.

That's embarrassing. Great first impression! Hailey's sister just saw me in nothing but my socks and underwear.

After I put on some clean clothes and the blush had left my cheeks I headed upstairs. Ms. Jackson was finishing setting up the table and the others were visiting in the living room. Everyone had shed their winter clothing, for the first time I got a good view of them all.

Jacob looked even smaller without his winter coat. The only fat he did have was a small pot belly. His brown hair was thinning. His thick rimmed glasses almost seemed cliché.

His wife Rachel was cliché in a whole different way. Her long blonde hair now free from her winter hat, fell several inches past her shoulders. Her white blouse was buttoned all the way up to her thin throat. It was baggy around her arms and small midsection, but the thin material strained against her immense breasts. They looked even larger than her Mother's. The outline of a white bra could slightly be seen through her shirt. Hands that donned ruby red nail polish, and a large wedding ring, rested on her hips. Hips that were hugged tightly by her denim jeans. In all, she had an incredibly nice hour glass figure.

Damn.

Leah had also shed her outer layer of clothing. Without her sunglasses I could see her face, identical to her twin sisters and similar to the rest of the Jackson family. Blue eyes, high cheek bones, thin nose, full lips, and a still highly feminine but clear cut jaw line. Her hair was shorter than her sisters, just above the shoulders. It was also blonde, but without her beanie off I noticed some light pink highlights. She wore a short sleeve shirt that looked like it was made to fit a twelve-year-old, and probably was, it said "Princess" across the chest. Her frame was small like her sisters, but unlike her sister her chest looked proportional to the rest of her body. The tightness of her shirt outlined her two small orbs. The V in her shirt was so low that it showed the little amount of cleavage her small breasts created.

That's strange. If their identical why does Rachel have a larger chest? Hhmmm, maybe they're just full of milk for the baby?

Leah's shirt was also short enough that it revealed her flat stomach and a pierced belly button. She also wore a tight leather skirt. If it were any shorter her ass cheeks would be hanging out the bottom. Speaking of her ass, it filled out the skirt nicely. The girl had done her squats. The short skirt showed off her thin smooth legs.

I compared Rachel and Leah to one another. Looking at them it was obvious they were twins. But at the same time they looked so different. I couldn't believe it.

"Come on everyone, let's sit at the table." Ms. Jackson said.

Leah bent down to pick up the baby. By habit my eyes went directly to her ass. Her skirt was low enough that I could see the two dimples in her lower back, what looked like the very beginning of an ass crack and a tattoo. It looked like a swirly type of pattern, just a few inches wide and couple inches tall.

Of course... she has a tramp stamp!

"Leah, will you say grace for us?" Ms. Jackson asked once we were all seated.

"Are you serious?" Leah responded.

"Fine, Rachel, would you pray for us?" Ms. Jackson asked.

"Of course Mother." Rachel answered.

We all bowed our heads. Rachel offered a beautiful prayer, but all I could think about were Leah's sex toys waiting one floor beneath us. After the prayer we passed platters around and dished food upon our plates.

"So Jacob, how is work?" Ms. Jackson asked.

"Fine." He answered. It didn't appear he had anything else to say.

"Are you used to breast feeding yet Rachel?" Ms. Jackson asked.

"Mother, I don't think that is appropriate dinner talk." She answered.

"Okay, fine. Leah, tell us what's new with your life." Ms. Jackson said.

Leah put her utensils on the table, "Everyone, I have a confession." She looked up at Hailey and smiled, "I saw your boyfriend in his underwear."

Everyone except for Jacob and myself began to laugh.

"And he has a smoking hot bod. Good job little sis." Leah continued, "And from what I could tell, it looks like he is pretty well endowed."

Rachel suppressed a laugh at this as well. Ms. Jackson and Hailey laughed heartily. I could feel my cheeks grow hot.

"Thanks Sis. How are things in that department for you?" Hailey asked.

"Oh you know, the usual. No one special." Leah answered.

"Enough about us, why don't you tell us about yourself." Rachel said, referring to me.

I briefly told them about my family, where I was from, hobbies, the normal things. Rachel asked me about my studies and what my plans were for the future. Even though she was only a few years older than me she acted is if she were many years my senior. Her husband remained relatively silent.

Leah asked questions more like, "How often do you work out?", and "How many girls did you go through before getting to my little sister?". I got the feeling that she enjoyed flirting with the line of what was appropriate and what was not. The rest of the family seemed accustomed to her behavior.

As the dinner went on I began to realize that the twins were not only different in the way they dressed, their personalities were drastically different as well. I saw little bits of Ms. Jackson in each of them. Rachel definitely dressed more like her Mother. And they shared a "professional" type vibe. But I had also seen Ms. Jackson be fun and spontaneous, like Leah.

Watching and talking to Rachel was like experiencing Mozart's 40th symphony. While Leah was more similar to a Def Leopard concert.

"Mom can I borrow a pair of boots for tomorrow?" Leah asked. Ms. Jackson gave her consent and Leah left to raid her mother's closet.

In Leah's absence the table grew uncomfortably quiet. I tried desperately to make conversation with Jacob, but to no avail. After a short time, Leah came marching back into the dining room.

"Okay Mom, who are you fucking?" Leah demanded.

"Leah, watch your language in front of the baby." Rachel said, covering her child's ears.

"What are you talking about?" Ms. Jackson asked.

"Going through your stuff I saw that you expanded your lingerie wardrobe. Come on Mom, you wouldn't buy that unless you wanted someone to see it. So who's the guy?" Leah reasoned.

I made eye contact with Ms. Jackson, then we quickly looked away. I looked down at my plate with a new feigned interest in my food.

I hope no one noticed that.

"I was not going to say anything until later, but you do have a certain glow about you Mother. One that wasn't there last time I visited." Rachel added.

I felt a surge of pride well up inside me. The fact that her daughter noticed a difference in her Mother must have meant I was doing something right.

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