tagMatureMs. Jackson Ch. 01

Ms. Jackson Ch. 01


Despite my regular trips the gym I struggled carrying this box. It was full of my girlfriend's shoes. It must have weighed over two hundred pounds, and there were three more boxes just like waiting for me in the truck bed.

"Put that box in the storage room, I won't need those till fall. But put the others in our room." Hailey commanded. I just grunted, not able to say anything.

Hailey and I had been together two years' now. We had met in our first year of college. I'm not sure what attracted her to me, she claims it was my charisma, but I don't know about that. I on the other hand had been blown away the first time I laid eyes on her. She had just finished her dance class when she walked into our General psychology course late. The whole class turned to watch her take her seat. Her long brown hair was tied up in a ponytail, showing off her immaculate bone structure. High cheek bones, defined jaw line, slender nose, and plump lips. It also didn't hurt that her spandex were skin tight. They showed off her long muscular legs and tight butt. I spent the rest of that semester trying to get into her pants, and along the way we sort of fell in love.

Now that we were both in the tail end of our degrees it did not leave a lot of time for work. So we were looking for a cheap place to live in order to save money while we worked on graduating. Hailey's Mom offered to let us live in her basement. Hailey loved the idea, I didn't. So here we are, moving into the Girlfriend's Mom's basement. It was really emasculating and I hated it.

However, I have to admit, it was the most logical choice. Hailey's Mom, Ms. Jackson's house was rather large. And since her divorce from her husband a year prior she was living in it all alone. There was a separate basement entrance. A spare bedroom and extra bath downstairs, the only thing that was missing was a kitchen, so we would have to share one upstairs. But Hailey and I would be at school most the time, and Ms. Jackson had an office job so I doubted we would run into one another often, if ever.

The best part was Ms. Jackson was willing to let us live here for free. As long as I helped out around the house/yard and we went to church with her on Sundays. Ms. Jackson was a very religious woman. When Hailey and I had first gotten together Ms. Jackson was not happy with the idea of her daughter and I living together before marriage. But Ms. Jackson is also a very smart woman, she knows when to choose her battles and eventually she let it go. I'm sure Hailey and I will get married someday, we're just not in a rush.

With all the boxes successfully moved in I let myself drop onto the sofa. It was a hot day and I was drained.

"Good job Chris, we got that done faster than I expected." Hailey said.

"Yeah, WE worked real hard." I said sarcastically. Hailey looked at me with a scowl. Then she leaned in towards me and gave a quick peck on the cheek.

"I know I didn't help much. But I'll reward you for it, promise." She told me with a wink. Then, lifting one leg gracefully into the air she straddled me. I reached around and took two handfuls of her ass through her booty shorts. Her pink bra could be seen through her thin white tank top. Her breasts were not porn star status, but they were definitely large for a dancer and her small frame, 28C's. They were sitting directly in front of my face. Blood slowly began to inflate my erection. The look on Hailey's face told me she could feel it. She put her arms around my neck and started grinding her pelvis into mine.

"It's kind of weird doing this in my Mother's basement, it makes me feel naughty." She said. Then she placed her lips on mine and slid her warm tongue into my mouth. My tongue wrestled with hers. I slid my hands up her arched back and clasped onto her shoulders. Then I used my new leverage to pull her body down into mine so I could grind into her with more pressure.

"Oohh..." she let out a soft moan. Then moved her mouth to my ear and began breathing heavily. I moved one hand to her chest and pushed against one of her breasts. She grabbed the bottom of my shirt and pulled it over my head, and threw it to the floor. She momentarily took a break from dry humping me to reach down and unbutton my shorts. Like a cat she slipped off my lap and onto her knees. Grabbing my shorts, she slid them down to my ankles. Now all that remained were my boxer briefs, my bulging penis clearly visible underneath them.

"Am I about to get what I think I'm about to get?" I asked excitedly. She simply nodded her head and ran her hands up my abs to my chest. They lingered there for a moment and then delicately headed south again. When they reached my bulge they stopped. Her delicate fingers squeezed the engorged member and tickled it with her fingernails. Then slowly, she started rolling my underwear down my thighs. First the swollen head was exposed, then inch by inch my now fully erected shaft was revealed. Free from my restricting boxers my member swayed slightly in the cool air.

Hailey wrapped one hand around the base of my shaft, the other hand reached down to massage her wettening pussy. She pulled my dick forward, leaned in and flicked the tip with her tongue. I was squirming now.

"Come on Hailey, enough teasing." I begged. She gave the head of my penis one more lick with the tip of her tongue and then opened wide to take me in... just then the door opened upstairs and someone entered.

"Hey Kido's, I'm home." Ms. Jackson hollered down the stairs. "Mind if I come down?"

Hailey franticly shoved my fully erect penis back into my briefs. I clumsily pulled my shorts up and reached for my shirt. Ms. Jackson stuck her head in the doorway seconds later.

"Woh, looks like you two have some organizing to do." She said, looking at all the boxes. "Why don't you two come up in a few minutes, I'll have dinner ready soon. And Chris dear, you do know your shirt is on backwards right?" I smiled sheepishly at her and she exited.

Hailey began laughing and I whispered, "You still owe me." After a cold shower I met Hailey and her Mother upstairs for dinner. The upper level was rather large, but only had a few rooms. One big kitchen, a living room with two sofas facing a flat screen, a sitting area that opened up into the dining room where a long rectangular table sat. And then a hallway which led to a master bedroom I had never seen. Ms. Jackson said we were fine to be upstairs whenever we wanted, she just asked we respect her privacy and stay out of her bedroom.

"Chris do you mind setting the table?" Ms. Jackson asked me. I dutifully began my task while Hailey and her Mother laid out the salad, and grilled chicken. It amazed me that Ms. Jackson worked full days and still had energy to come home and cook.

"Hailey, you say grace for us." Ms. Jackson said. We bowed our heads and Hailey offered a short prayer. After we began dishing our food and Hailey started telling her Mother how she planned to decorate the downstairs. I took opportunity to listen and look at the two of them interact.

In many ways Hailey looked a lot like her Mom. And I was glad, I hoped Hailey would age as well as her mother, Ms. Jackson was a stunningly good looking woman. Hailey got her bone structure from her Mother. Ms. Jackson too had very high set cheek bones, slender nose and a well cut jaw line. Her face was beginning to show the hint of wrinkles, but it wasn't bad, after all she was in her late 40's. Her lips were plump like her daughters, perhaps slightly more full actually. I wondered if she had injections, either way, they looked very good. Her eyes were the same crystal blue with long luscious lashes. Hailey had also inherited her mother's frame. She was skinny with a slim waist. But there were also some differences.

Unlike her daughter, she had blonde hair. And she didn't wear it quite as long, it fell just past her shoulders when she wore it down, tonight it was pulled back in a bun. While Hailey weighed 115 pounds I would have guessed her mom weighed closer to 140 lbs. Don't be confused, she did not look heavier than her daughter, she was just a few inches taller. I would bet just under six feet, and all the rest of the extra weight was in her bra. Her breasts were much larger than her daughters. I forget how it came up, but Hailey had told me once her Mother wore a 32DD. She was a modest woman; rarely did she wear anything that showed them off. Tonight was no exception. Sha had on a gray sweater that matched her dark skirt. My eyes traveled down the sharp lines of her jaw, down her thin neck and then to the large round melons that stretched at the fabric of her sweater, only to jut back in once you reached her thin waist.

"Earth to Chris, do you want a roll or not?" Hailey prodded me.

"Oh yeah, thanks." I answered, taking a roll from the basket she was holding.

"Well I hope you two love it here. It is nice to have you back home." Ms. Jackson said with a big smile.

We did love it. It was of course amazing not to have rent to worry about. And an extra perk that I had not taken into consideration when we first moved in was all the home cooked meals. The first time our normal routine was broken up happened our first Saturday there. I asked Hailey to go to the gym with me but she said she would rather sleep in. So I slipped my running shoes on and headed to the gym alone. The parking lot was pretty full and I had to park pretty far away. Eventually I made it inside. I hung my keys on the rack next to the door and looked up at the row of treadmills. Most of them were taken. My eyes did a sweep of the people on them, men and women of all shapes and sizes. One woman caught my attention immediately, Ms. Jackson.

She had on pink Nike running shoes, ankle long black spandex showed the curves in her muscular legs. They also hugged her round ass, which gave almost no jiggle as she jogged. It looked solid. On top she had a pink sports bra, to match the shoes and a baggy white tank top over that was cut in on the back and had a fairly low neck line. Her toned arms pumped back and forth. Despite the pink sports bra her breasts lurched up and down as she jogged. Colliding into one another as they came up, creating a mountain of cleavage with each step. Her blonde hair, tied in a ponytail swung from side to side. She usually did not wear much makeup, but at the gym she wore none. Without it she looked a couple years older, still great for her age, just an older version of Hailey. After I had enjoyed the site of her for a few moments I approached.

As I got closer she noticed me, smiled and took her headphone out of her ears.

"Hey Ms. Jackson, I didn't know you came here." I said.

"Yeah.. I try to come... every day..." She said, slightly out of breath. She turned the speed down on her machine and started walking. Which did not do much to calm the bouncing of her large breasts. It took all my will power to keep my eyes on her face.

"Me too. How come this is the first time I've seen you?" I asked.

"I usually come before work, so I imagine you are at school at that time. But good for you for finding the time to work out. It really shows." She complimented me. I blushed, remembering that I was in a tank top.

"Uh, thanks. You look good too." I said honestly, but it caused me to blush even more. She just looked down at me and smiled. A single bead of sweat formed on her neck and began moving downward. I tried to resist but my eyes followed its progress down. Down until it was lost in the cavern created by her massive chest.

"Thank you dear. Have a good work out." She said and put her headphones back in. My sign to move along. I headed to the free weights and began my workout. Every now and then I risked a glance across the gym to where Ms. Jackson was. She moved from the treadmill to the donkey kick machine. Leaning forward she kicked one leg back, which was resisted with weights. The motion caused her glutes to contract. From there she moved to a machine where she sat and squeezed her legs together. I knew she was my girlfriends Mother, but I couldn't help but day dream of how sexual she looked in all of those positions. Realizing I was moving through my routine at half the speed I normally did I decided to concentrate.

I moved to the bench press and quickly did some sets. I added some weight to each side. Resuming my lying position, I moved the weight off the rack and did a couple reps. My chest really began to burn on my fourth rep down and I struggled to get it up. Just then a female set of hands grabbed hold of the bar and helped me get it the rest of the way up.

"How many more you got left?" Ms. Jackson's voice asked.

"At least three more.." I grunted. She encouraged me to keep going. I did the last few reps with her help. Then I let the bar fall heavily onto the rack.

"Hey thanks, I definitely could not have done those last ones without you." I said.

"No problem. Besides It wasn't completely selfless. Would you mind spotting me on the squat rack? I just really want to make sure my form is good." She answered.

"Oh sure, of course." I said. I followed behind her to the squat rack. My eyes glued to her muscular ass as she walked. Then I realized we were standing in front of a giant mirror and she could probably see me, I looked up quickly.

"Just make sure my feet stay shoulder width apart, my back is straight, and that I am going down past ninety degrees." She instructed me. She obviously knew what she was doing, "And while you spot me stand directly behind me and keep your hands on the underneath of my ribcage to help me lift up. But don't help too much, make me work for it."

She got situated and lifted the bar off the rack. I took my place behind her and reached around her sides and placed my hands on the bottom of her ribcage. If I had moved my hands just a couple inches up I could have felt the curvature of her breasts. She bent at the knees and squatted down, keeping her back straight she thrust her butt backwards. I copied her motion and followed her down, trying to keep some space between our bodies. But at the bottom of her squat it was impossible, her firm ass cheeks brushed against my crotch.

She shot back up. Then she repeated the motion nine more times. Each time her butt pushed against my crotch. I was so thankful that I had worn my compression shorts because by the end of her first set I had a raging hard on. Could she feel it? I don't know, I hoped not. By now sweat droplets formed everywhere her skin was exposed. Each time she squatted her glutes, quads and calves flexed. On top of that the reflection of the mirror gave me the front angle as well, each time she dropped down I got a flash of her cleavage. It was too much, and by the end of her final set my raging hard on was throbbing.

"Thanks for the spot. I'm going to do some core and then I think I'm done for the day." She told me.

"Yeah I think I'm done for the day too."

"Hey, why don't we just carpool from now on?" she asked.

"Yeah, no sense in driving two cars."

"Okay, sounds good. I'll see you at home." She said.

We did carpool from then on. We never missed a Saturday. Sometimes Hailey came with us, but most of the time she chose to sleep instead. When Hailey didn't come Ms. Jackson would always ask me to spot her for certain lifts. I noticed she never went without makeup again after that first time. And I was sure to never forget the compression shorts. We talked on the drives to and from the gym. I told her about school. We talked about Hailey. She told me how things were at the office. She worked for a company that sold health and beauty products. Meal shakes, bath soap, antiaging cream, etc. Which made sense, Ms. Jackson was obsessed with living healthy and taking care of her body. Every now and then she told me about the guys she was dating.

We were getting to know each other better. But it never felt like a 'friend to friend' thing. It was more like an authority figure giving advice and counseling to a younger person. She definitely treated me like a kid. I often found myself looking forward to seeing her when I got home. But when I caught myself thinking of Ms. Jackson I mentally scolded myself and directed my thoughts either back to the lecture or towards Hailey.

"You're home late." Hailey said to me as I kicked off my shoes at our bedside.

"Sorry. I was at the library writing a paper." I shed my shirt and pants and collapsed into bed next to her. I snuggled up next to her and wrapped an arm around her torso. She was braless, wearing one of my t-shirts and panties. I slid my hand underneath her shirt and grabbed a handful of boob. She slapped my hand away.

"Your hands are freezing!" she hissed. I laughed.

"Well help me warm them up. You know it's been a while. Want to fool around?" I asked her and kissed the back of her neck.

"I'm pretty tired. How about tomorrow?" she asked.

"But were just as busy tomorrow." My hand moved back to her breast. They must have warmed by now because she didn't slap it away.

"Fine. But just a quick hand job. I have to get up early in the morning." She rolled over so that she was facing me. Then she reached down and her hand quickly slipped underneath the waistband of my underwear. She allowed me to continue massaging her breasts as she fondled my balls. Then she grabbed hold of my soft dick and gave it a squeeze.

"Come on, get hard for me babe." She ordered me. With her free hand she started massaging her other breast, the one I was neglecting. She knew I liked that.

Slowly my limp dick began to grow and expand until her small hand could hardly wrap all the way around it. She rolled back over, reached over to a bottle of lotion on her night stand, shot two squirts into her hand and then was back.

With a hand full of lotion, she easily slid all the way along all seven plus inches of my cock. She pumped up and down, and twisted her hand like a cork screw while she did. My dick was soon lathered in the lotion. She varied her pace from time to time. She slowed, squeezing harder as she did. Then she picked up the pace again and stroked me fast. Back and forth.

"Ahhh" a soft moan escaped my lips.

"That's it, cum for me babe, Cum for me." She whispered hotly into my ear and increased her pumping speed. I could feel it coming, like an eruption it started in my balls and sent a hot load up my shaft, out my head and onto my stomach. Hailey slowed her pace but kept stroking me. After the initial load a few smaller squirts of jizz seeped out of the head of my penis.

"Are you done?" Hailey asked. Her sultry voice replaced with a normal one now.


She kissed me quick on the mouth and rolled over. "That must be a record time. Goodnight babe."

"Goodnight Hailey." I replied. I took a pillow case off one of the pillows and used it to wipe up my jizz, then discarded it onto the floor. I laid my head back and closed my eyes. Hailey was right, it was a record time for getting me off. I decided to keep to myself that while she was jacking me off I was fantasizing it was her Mom lying next to me, stroking my cock.

The next time I came home that late I found Hailey was already asleep. I didn't blame her. She had a busy schedule, so did I. It just seemed the free time we did have in our schedules never overlapped. I brushed my teeth, got ready for bed and then snuggled in under the covers next to Hailey's warm body. I was just about to drift off into dream land when I heard people's footsteps on the floor above us.

One went "click, clack". That must be Ms. Jackson's heels. The other were much heavier, "Thump, thump". That must be her date. I forget his name but she had been seeing this guy for the longest out of all of them. I could hear muffled voices, and every now and then the man would give a hearty laugh.

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byjeffincognito© 30 comments/ 324436 views/ 529 favorites

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