Age Gap

Candice

After several seconds of staring at me with hooded eyes, the boy cleared his throat and reached out his hand.

"Hi Mrs, Miller, you may not remember me, I am Courtney's friend, we met once at the annual cook-off a couple of years ago."

I examined the boy closely but he did not look familiar.

Seeing my confused expression the boy shifted from one foot to the other on my doorstep and tried again, "I am Jackson, Lily Holbrooks is my mother."

Letting my guard down I smiled and took the boys' extended hand, "Oh yes, Lily's boy, you must be here for Courtney, she just went running a few errands but will be back shortly, come in."

Escorting Jackson to the living room, I told him to have a seat and asked him if he would like anything to drink and he requested lemonade. Sitting the cup and coaster down on the end table I took a seat across from him wondering how I should entertain this unexpected guest.

"So, what has your mother been up to lately," I asked, although I could really care less about Lily and her snobbish attitude.

The boy took a sip of his lemonade and smiled, "It tastes just like you made it at the cook-off," he said ignoring my question. His stare was incessant as he examined me with an intensity that made me pause.

Is he checking me out? I thought in disbelief. No, he is here for Courtney.

Shaking off an uneasy feeling, I tucked a piece of hair behind my ear and bit my lower lip. Clearing my throat I gave off a forced laugh, "Is my lemonade that memorable?"

He gave it another sip, not breaking his gaze for a second. Setting the cup back on its coaster he smiled," It is a very special recipe."

The way he was looking at me, I was almost certain he wasn't talking about the lemonade. I started to regret my decision for letting this young boy into my home.

He couldn't be more than 21-years-old, standing over six-foot-tall, he had what I would call a swimmers body. His eyes were dark, so dark they appeared black and most women would envy his eye-lashes. He was very attractive and any young girl would appreciate it, but I was old enough to be his mother, in fact, I was two years older than his actual mother.

I pulled out my cell phone and sent Courtney a quick message, letting her know that her friend was here and to hurry up with errands. She quickly texts back saying she would return within 30 minutes. I relayed that information to the boy, sliding over the remote to the television and got up to go back to my home office.

"I am sorry I cannot keep you company, but I have some important work to catch up with," I said, "if you need anything I will be just down the hall to the left"

Jack

As I watch my dream woman walk away, hips swaying in a pair of tight jeans, I repositioned the bulge in my pants. I didn't move from my seat, because I needed to get my heart to stop slamming against my chest and settle my pacing mind.

I met Candice seven years ago when I was still a sophomore in high school; unlike my mother, she was very active in her daughter's schooling. She participated in every teacher's conference, every sporting event, and was on the PTA.

I would never forget the day she knocked on our door, wearing a plain white t-shirt and tight flower-patterned leggings, clutching a huge folder to her chest, hiding her large tits. Her smile was blinding when I answered the door.

"You must be Jackson," she said, "I'm Courtney's mom, I am here to speak to your mother, is she in."

Stammering I gripped the knob tightly.

She's so fucking beautiful, I thought.

"Lily," I called out to my mother.

"Jackson, I am busy, what is it?"

"You have a visitor," I yelled. I could see Courtney's mother frown of disapproval when I called my mother by her first name. Lily didn't like being referred to as a mother, she said it was unnatural and made her feel old.

"Candice Clark," Lily gasped, coming to stand next to me. "Is that really you?"

"Do we know each other," Candice said curiously, peering closely at Lily trying to place where she knew her.

"It's me, Lily Holbrooks," she said. "We went to Morehill together, I was a couple of classes behind you but we both dated Danny...you remember Danny, Danny Miller?"

I watched as Candice smile slowly slipped from her face and for a short period, almost as if I imagined it, a flash of anger replaced the smile.

"Oh, yes," Candice said, her smile back in place, "I remember you now... and so does Danny." She adjusted her hand and it was hard not to miss the huge diamond on her ring finger.

"Where are my manners," said Lily, her voice tensed, "come in, have a seat."

*****

"What brings you to my home," asked Lily, crossing her bare legs, showing off her thighs. I watched my mother size up Candice with a look of disdain. She always looked down at anyone that didn't come from a wealthy background and felt that she was superior to anyone that couldn't stand up to the good old' Holbrook's legacy, even though she had nothing to do with my grandfather's business.

Reaching inside her folder, Candice pulled out a flyer and handed it to my mother. "I am asking all parents to participate in this new charitable event to help with the school's scholarship program for underprivileged children," she said with excitement, ignoring the disinterested look on Lily's face, she continued.

"It will not only bring in funds to the scholarship, but it will help establish an after school program that will allow the kids the opportunity to participate in sports and other extra-curriculum activities, fostering equality amongst all students."

I couldn't help but admire Candice as she went on describing the program. Her hands were expressive and when she started shaking her head, loose strands of hair fell from her sloppy ponytail. I wanted so much to reach out and fix her hair in place but I stayed silent while watching the transaction.

Throwing her head back in laughter, Lily tossed the flyer carelessly on the coffee table. "Candice, do you seriously think that those children have a shot in life just because of a few measly donations?"

Crossing her hands over her chest she continued, "Why would you waste time on a lost cause, I can't believe this is what you've been up to all of these years."

Picking the paper off the coffee table calmly, Candice placed the flyer back in her folder. "So, I see you haven't changed in all of these years," she said, her voice low with controlled anger. She looked like she wanted to say more, but she glanced at me and fixed her face. Standing up to leave she made one more last pitch to Lily. "Well, you are still welcomed to attend the festival we're having to raise the funds."

She left with so much class that it took my breath away. My mother usually gets under people skin causing them to lose their cool, but Candice was different, she handled my mother very well.

********

That night I had the most intense wet dream ever, starring Courtney's mother. She was still in that white t-shirt, but it was drenched in water and her nipples were visible under the fabric. Her hair was soaking wet, still in a messy ponytail, strands plastered to her face. Those tight ass leggings left no room to the imagination, hugging all of her curves.

She started massaging her nipples, giving me that beautiful smile. Little moans escaped her mouth as she pinched her nipples. "Do you want to make a donation," she asked, spreading her legs.

As I was about to reach out and touch her, my alarm went off and I was squirting cum all over myself.

"FUCK," I shouted, angry at the interruption, grabbing a couple of tissues from my nightstand to wipe myself clean.

When I arrived at school that morning I made every effort to figure out who Courtney was. Turned out she was in one of my classes and sat a couple of seats ahead of me. She was a pretty girl, with long brown hair like her mother's but it was neater, every strand in its place. She stared up at me with wide eyes when I approached her, which wasn't surprising because I barely made an effort to socialize at school, even though I was aware of my unwanted popularity which came from having a well-known last name.

Courtney was an overachiever that participated in almost every school program there was to offer. She was very active; a cheerleader, volleyball player, on the drama department as part of the stage crew, and as it turned out a shoo-in for homecoming queen. All of this information came from my childhood friend Dennis who was surprised that I didn't know who she was.

"Are you interested in her or something," he asked suspiciously.

"No," I said, "I just need to ask her a question that is all," not giving him any further information.

"You're Courtney right," I said turning my attention to Candice's daughter.

"Yes," she said slowly, " And you are Jackson Holbrooks, William Holbrooks grandson, and only heir to the biggest retail company in all major states." She grinned at me. "What can I do for you?"

Although Courtney had a cute smile, it didn't hit me as her mothers. "I heard that you sit as vice-president on the student's council and I wanted to know how I could get more involved."

She squinted at me with disbelief and seemed like she was about to grill me right there on the spot, but instead, she smiled up at me and took out a large stack of papers and handed it to me, "you can start, by hanging these up around the school and all over town."

I looked down at the flyers, and they described the charitable event Candice spoke of the day before and I felt my heart pounding in anticipation.

*****

The more involved I got in school activities, the more chances I got to see Candice. She showed up to school dances, sporting events, field trips and she never missed one of Courtney's activities. I was also present during all of Courtney's events and it got to the point where she point-blankly told me;

"I have someone I like already."

"So do I," I said, thinking about her mom.

It was getting past the point of obsession with me. I knew that nothing could come out of my day-dreaming because it was no secret that Candice was very much in love with her well-known award-winning doctor husband, Danny Miller, and I was just some entitled rich high schooler. I knew it was irrational to feel some kind of a way about it, but I hated the thought that someone else's hands but mine got the chance to explore that hot body.

Every time I got a glimpse of her, I would have a long jerk-off session that same night, remembering her every gesture, and smile. In junior year, I decided to distract myself and finally accept one of the many offers I got from the girls at school. Her name was Amanda, a short, plump girl, with a pixie hair cut. She was surprised when I accepted her invitation to go bowling and it didn't take me long to find out she wasn't all that popular. I didn't care who I dated, I just needed to get my mind off Candice fast.

After our first date, while driving her home, she started rubbing my cock through my jeans. Surprised, I swerved and quickly removed her hand.

"Don't do that," I said with a bit too much force.

Parked in front of her two-story house, I looked over at her sitting in the passenger seat, and saw that she was weeping.

Feeling guilty, I reached over and rubbed her back. "Hey, Hey," I said softly, "I'm sorry, it's just that I was driving and didn't want to cause an accident."

She turned her big brown eyes toward me, "You didn't like me touching you, I could tell, you must think I'm disgusting."

"I wouldn't have accepted the date if I thought that," I said reassuringly, feeling a bit of pressure on my chest. "I really don't want to sound cliche, but I think taking your time with a person you like is important." I hate seeing a female cry and was willing to say anything to get her to stop.

"Really," she said softly, looking at me hopefully. "...but it's no secret to everyone that you have it hot for Courtney Miller, she's popular, beautiful, smart and I am just the fat girl"

"Don't put yourself down like that," I said pushing down my annoyance," you have many great qualities."

She looked at me skeptically, "But you're a Holbrooks, you can have any girl you want, why did you go on a date with me?" She searched my eyes for an answer as I tried to rack my brain for what I knew about her but I came up short.

I deflected," Being a Holbrooks comes with a whole set of its own problems," I said, thinking about the pressure Lily and my grandfather put on me to take part in the family business.

Amanda drew closer to me, tilting her head up for a kiss,"...so do you really like me," she muttered.

Staring down at Amanda's cute face, and luscious lips I couldn't kick Candice from my mind.

Taking the plunge, I kissed Amanda passionately, holding her head between my hands, exploring her mouth hungrily. I knew it was wrong to kiss one woman and be thinking about another but I couldn't help myself, having stored up these emotions for over a year, I needed an outlet. Eyes closed, I reached out to grab Amanda's breast and I squeezed them a bit too rough, she let out a little scream against my lips. I started to remove my hand but she grabbed it and placed it back on her chest, shaking her head.

"Do it again," she said smiling slowly. Growling, I kissed her roughly and squeezed her tits hard. I felt my cock press uncomfortably against my pants as I imagined I was kissing Candice. I felt fiddling with my zipper and after a couple of awkward pulls, she freed my cock from the slit in my boxers. I didn't have to look to know that it was standing up straight. I felt her hands grip my shaft, circling the tip with her fingers. I stopped kissing her and reached down to adjust my seatback. Her hand was stroking me up and down and I felt my cock about to explode.

"Do you like that," she asked, and I felt her fingers lightly squeezing my balls.

"What do you think," I said grunting loudly, my hands beneath my head, enjoying the feeling. And before I could react, I felt her mouth on my cock. Eyes flying open in surprise, I felt a sensation that I never felt engulfed me. She circled the tip of my cock with her hot-wet tongue, using quick little strokes. My heart started beating fast when I saw her head go straight down to the base of my cock. I can honestly say, I was not thinking about Candice at that moment.

"Holy_" I groaned, gripping the back of her head. Instinctively, I pushed her head down my cock and I lifted my hips from the seat thrusting into her hot little mouth. I felt her gagging a little and my heart started going wild. My mind was all over the place as Amanda's tongue stroked up and down my cock causing me to moan uncontrollably, I never had a blow job before and it was driving me insane.

I felt my body tense up and I had the most intense orgasm I ever had as I felt my lower regions spasm. I ejaculated right into Amanda's mouth and she swallowed it down in one huge gulp. She kept licking me afterward and my body shook from the sensitivity. Pulling her head up to stop I sat there waiting for my heart to calm down.

Amanda looked at me with a satisfied grin, cleaning the corners of her mouth with the back of her hand. "I love you, Jackson," she said looking at me with adoration. I stared back at her with shock and I didn't know what to say so I just nodded my head and waited for her to exit the car.