Age Gap

Jack

After the first night with Nina, we start hooking up quite a bit. I found out that she had a rare form of narcolepsy which made her excessively tired. Bartending was the only thing that kept her energy level up, and she did not report her condition to her boss. Nina was everything a man could hope for, and I imagined myself falling for her but I found myself still stuck on Candice.

When will this childhood infatuation ever end

, I thought.

The night I lost my virginity was supposed to be the turning point from being a teenager, just wet behind his ears, to a man with a newfound outlook on life.

It was like any other day, after preparing hours for the exams, I would meet up at her apartment to wind down. We would sit on her bed, watching the T.V., stuffing our faces with unhealthy snacks. Afterward, we would start making out, and as always, her hot tongue will feel amazing against mine. The smell of warm lavender soothed my nerves and her hands felt soft while caressing the back of my neck.

"Fuck me, Jackson," she said this time, reaching to caress my cock which was straining against the fabric of my jeans. She used her tongue to lick around my mouth, and her teeth bit down ever-so-gently at my lower lip, making my cock involuntarily jump.

I was ready to take the plunge and something came over me and with a flash, I pushed her down and laid on top of her, legs came up and wrapped around me. I stared down at her and she was looking at me with knowing eyes. I pressed my hardness against her, and I swear, I could feel the warmth through the layers of our clothes. I moved my hips and started grinding myself into her slowly.

"MMM," she let out a sexy little moan, and my desire started to grow. I leaned back impatiently and started fumbling with the buttons on my shirt. I could not stop myself from panting, and I felt her soft hands come up to help assist me with my shirt.

"Calm down Jackson," she said, rubbing my bare chest, she leaned forward to place kisses around my nipple and she bit down playfully. "What are you a virgin or something?"

Ice water ran down my spine. I tensed up and rolled off her, my cock slowly retreating.

"Oh no," she said, looking at me with surprise, "this is your first time?"

I hated to admit it, but there was no reason to lie. I told her about my short time with Amanda and that I never experienced intercourse.

"You poor boy," she said. She reached down and caressed my cock again. "I'm going to take care of this situation."

She leaned over and placed her hot tongue on the side of my neck before biting down, I felt the pain, but her hand on my rising cock kept me distracted.

"Nina," I moaned.

"Yes, I will make sure you will never forget your first time," she said, her hot breath against my ear sending shivers down my spine. She bit down on my earlobe and started unzipping my pants. I pushed myself up, moving my hips side to side as she struggled to pull them off me. My underwear came next and my cock was standing up straight, and Nina licked her lips.

"How can this be neglected for such a long time," she said, a look of disbelief on her face. Without warning, she pressed her lips against the head of my cock head, and her tongue flicked out to lick up the pre-cum. Her mouth was soft and warm and I clenched my fist, attempting to get control of my body. Nina looked up at me with her cute face, her eyes were big and round, indicating innocence, but her expression was experienced. While looking at me, her tongue flickered over my cock, teasing me.

"God that feels good," I heard myself say, my head feeling somewhere above me. The sensations were traveling throughout my body and my leg started bouncing up and down. Nina laughed at that and placed one of her hands on my leg to hold it down.

"This has got to be the best-looking cock I've ever seen," she said, before stuffing my dick down her throat.

"Shit," I screamed. Her head bobbed up and down my shaft and I had to catch myself from cumming instantly.

She briefly pulled away and I was in for a shock when she spat on cock, the huge wad slid down my shaft and she immediately followed it with her mouth, her eyes still on my face. Embarrassed that I enjoyed that, I closed my eyes to hide my expression.

She pulled away and my eyes flew open to watch her slowly take off her clothes. She stood before me, naked, covered in all her tattoos, her breast perky, her hips flared out slightly, and her mound had a strip of hair down the middle, but the rest was bare.

"You're beautiful," I said, watching her crawl back on the bed, giving me a slow smile. I did not notice when she grabbed the condom, but she was tearing it open and hovered it over my cock.

"Hopefully this will fit," she said, "Never thought I would need anything bigger." Pinching the head of the condom, she slowly rolled it down my cock. The sensation was different, but I was too horny to care.

I was laying on my back, my cock pointed toward the ceiling, and Nina climbed on top of me and slowly lowered herself on me. Inch by inch, I entered her, and it felt different from a mouth. Tight walls closed over me and I bit my lip so I wouldn't make any sounds.

"Look at me Jackson," she said, leaning down she placed a kiss on my chin before arching back, her hands bracing against each side of my legs and she started moving her hips.

"I said don't close your eyes, Jackson," she said. Her tits were bouncing up and down as she rode my cock.

"Fuck me back Jackson," she said.

I started moving my hips and thrust upward and the sensation felt so good that I started moving faster.

"MMM."

Our breaths were coming faster and my body couldn't handle it any longer. With a growl, I flipped her over and started pushing into her slick, hot, cave. She closed her eyes.

"Don't close your eyes, Nina."

"Are you sure you are a virgin Jackson?"

I plunged into her faster, my hips started having a mind of their own and I was jackhammering her insides. Her hands came up and held onto my back, and she started shaking beneath me.

"Yes, Jackson that's it"

We one last thrust, an orgasm tore from me and I felt myself cumming. It was an odd feeling, cumming inside a pussy, even though I had a condom on. I started smiling and Nina grinned while reaching around to pat my butt.

"Good boy," she said.

Involuntarily an image of Candice flashed through my brain. I slipped out of Nina and frowned.

Why am I still thinking about her

, I thought,

especially right now?

Candice

Two years have passed since Danny died and I still could not bring myself to get rid of his things. Little reminders were everywhere around the house, even the last toothbrush he used was still in its holder. Courtney long gave up trying to convince me to donate his items; she knew that I was not ready. I was not sure if I would ever be prepared for that day.

It was one of those moments when the grief would sneak up on me after putting in so much work to put it behind me. Tears flooded my eyes as I remembered our vows, and how Danny promised me that he would always be the one taking out the garbage.

I started smiling through my years, as I pushed down the plastic bag in the packed bin. Every time I took out the trash, I would think about my husband and how he was true to his word. Head down I turned to go back in the house when my neighbor, Samantha, poked her head out the door and waved me over.

"I heard you are going to help plan the annual cookout," she said, looking at me with pity.

Does it look like I've been crying

, I thought.

"Yes," I said, not surprised that she heard about it. Samatha was the cliche nosy neighbor who had her ears opened to everything. She was kind and was always willing to lend a helping hand, but I suspected that was her way of finding out more information on the people in the community.

"Did you hear that a Holbrook's will be attending?"

I bit the inside of my cheek and shook my head no. I did not want to be standing there gossiping, I wanted to crawl back into my bed and curl up into a ball, with Danny's t-shirt on and cry my eyes out.

"Well, I heard that they are going to be making a sizable donation since they have missed the last two cookouts."

My ears perked up, "Where did you hear about this?'

"Oh you know, here and there," she said and leaned closer and whispered, "That grandson is dating a gothic-looking stripper."

"Which grandson," I asked, not caring.

"Jackson Holbrooks."

The name did not ring a bell.

"It was all in last week's rag," she said with a smug look on her face. "That golden child is a menace, and if we could just find out who his father is_."

"Samantha, that is enough."

I was irritated and did not want to discuss it any further.

"Well it's true no one knows the boy's father," she muttered, pulling back. "I just wanted to make sure you did not need anything before the event, you know I am always willing to help."

"Thanks, Samantha, but I got everything covered."

"I am here if you need me," she said, stepping back into her house and closing the door. I was sure she was still peeking out the viewfinder.

With a sigh, I walked back toward my house and closed the door.

***

"What do you mean you won't be able to make it," I said, trying to hide my disappointment.

I was on the phone with my daughter, who decided to go to college 70 miles away from home. She was studying to be a doctor, just like her father.

"Professor Turwick is coming out of retirement and will be doing a lecture that day, I don't want to miss it."

"Won't it be recorded," I asked, feeling silly for even inquiring. Professor Turwick was my daughter's hero. When other children admired sports figures, actors, and artists; my daughter looked up to scientists, astronomers, and doctors.

"Forget I asked that," I said with a sigh. "When will you be able to come home?"

"Don't worry mom, I will be there for the cleanup."

"Just come home... and safe."

"Are you kidding," she said, "I wouldn't miss the annual cookout clean up for the world."

I laughed at my daughter's silliness. If there was one thing that helped me out of depression, it was my daughter's ability to make me smile over the little things.

After speaking with Courtney, I went over the plans for the cook-out. I made sure to extend my list of attendees just in case there were more people that showed up. The entertainment was already booked, and the donation center was set, so the only thing I needed to do was prepare for the event.

"Time to turn lemons into lemonade," I said to myself.

Jack

It's been a bit over a year since I visited home, I agreed to come back at my mother's insistence. She wanted me to be a representative for the family at the community annual cookout because she could not be bothered to be seen with the 'common folk.

"Why not just give a donation through the foundation like you do each year," I asked her suspiciously.

"There have been rumors swirling that we just throw money at problems, just show your face, hold up the donation check and you can go back to playing with your little toy."

"She's not a toy, mother," I said, feeling my face flush with frustration. Someone had leaked pictures of me with Nina and it's been the talk of the town. Nina did not seem to mind, when I apologized to her, saying that she felt like a celebrity, but something about it rubbed me the wrong way.

"You know not to call me that," she continued, her voice sounding far off. "Be sure to take many pictures for the press and don't bring that girl with you, bye honey."

She hung up before I could respond. I placed the phone in my pocket and took out the key to my new apartment while balancing grocery bags in my hands. I had just gone shopping, promising myself to learn how to cook instead of ordering out and eating prepackaged garbage. The apartment I moved into was small but had a decent-sized kitchen that I intended to put to use. When I told Nina about this she teased me, saying that I was not a normal college student, who spent their free time partying and drinking until they were passed out drunk.

"That's a stereotype," I had told her, leaning down to kiss her full lips.

"You just don't want to admit it," she said, looping her arms around my neck, and deepening the kiss.

"Admit what," I said, pulling back for air.

"You're like an old person," she said, "you don't act your age."

"That's because I'm mature."

"You should live a little more."

"I do live," I said, "I have goals and I intend to achieve them through hard work and not succeed due to nepotism."

"I just do not understand you," she said with a yawn, crawling on my new full-sized bed. "You have everything but you are just throwing it all away."

"It's not everything when the person handing it to you has strings attached." I looked over and realized that she fell asleep.

Shaking my head at the memory, I started loading my fridge and thinking about the annual cookout. I was not against giving back to the community, it had become a passion of mine to volunteer my time. What I didn't like was being some kind of puppet. My grandfather has always been distant from me, and showed that he did not care; however, I was his only living descendant and he would refuse to die before handing his precious company to anyone that was not family. Attending events was another way to draw me closer to the business and show the board that I was a willing participant, and would be next in line to run the company.

Leaving out the protein shake I brought from the store, after unloading my groceries, I took a sip and sat on my kitchen stool.

Here's to the cookout.

***

Candice

As promised, the weather was perfect, with just enough breeze to ward off the heat. The cookout was at Grand Park, and the setup was perfect, the picnic benches had white and gray table cloths, the live band had their stage set and ready to go, several food contributions were made, and the barbecue grills were loaded.

"Hey Candy-Dandy," said Michael, while coming up to me, we embraced briefly and he smiled his pearly whites at me. "You look absolutely breathtaking, darling and what perfume you are wearing it smells divine?."

"You don't look so bad yourself," I said surveying Danny's best friend, who stood a foot taller than me, his hair down to his shoulders, he wore wire-rim glasses which only added to his attractiveness.

"How have you been holding up lately," he asked, his eyes filled with concern.

I shrugged. "You know, just keeping myself busy has helped, I only cry once every three hours now."

The joke didn't go over well and we both silently looked on as guests started trickling in.

"Looks like we will have more people than the last two years," he commented gripping his stomach, "I heard that lady Jay is bringing her stuffing and I don't want to miss out before it's gone."

"Oh you better hover around the table for that, last year people were fighting over the last bits."

My nosy neighbor Samantha was headed our way with a determined look on her face.

"Well hate to leave you here but I see someone by the grills that need my help," Michael said, making a quick dash before Samatha could pester him. Everyone knew that Samantha had a crush on Michael and he did everything he could to avoid contact with her.

"Wasn't that Michael just now," she asked. She was wearing a wide brim hat, with tinted shades and a bright shade of lipstick.

"You look nice today," I said, redirecting her attention.

"Oh, thank you," she said, smoothing down her floral print dress with her hands and giving me a satisfied smile, "I got this on sale at the Holbrook's department store, they are having fewer and fewer discounts lately, I heard they may be having financial difficulties."

Can't you just go one minute without spreading gossip

, I thought.

"Anyways, I thought you might need some help so I came early," she said, looking toward Michael. "Perhaps at the grills."

I was going to turn her down but decided to seize the opportunity. "Well now that you've mentioned it, one of the attendants at the child's play area could not make it," I said, hiding my smirk. "You would be a great service if you could attend there and make sure none of the children wander off."

Her face fell but she quickly replaced it with a smile. "Of course...children, I would be happy to help, where should I go?"

I gave Samantha directions and started to greet the guests as they arrived. I was going through the motions but my heart was hurting because I remembered coming to this event with Danny and we would have so much fun playing the charity games and mingling with our friends. Now, it felt meaningless, while everyone was smiling and enjoying themselves, I felt as if my world was frozen.

"I need your help," said Leah, walking toward me from the raffle table.

"What can I do?"

"I need you to pull the raffle numbers and give away the prizes."

"I can do that," I said, grateful for my friend not calling me out for being such a downer.

I walked over to the table and picked up the mic.

"Thank you, everyone, for coming today, I hope you are having a good time," I said looking out at the sea of familiar faces. "So far we have raised $59,000 dollars and the day has just begun."

I heard a round of applause.

"I am going to call out the first three raffle numbers, when I do come up and retrieve your prize," I said, circling the ticket turner "this prize is for dinner for two at Rafael's...you can't possibly be thinking about food right now, but imagine a nice candlelit dinner at one of the most prestigious restaurants in our town and now imagine not paying those crazy prices."

I was rambling.

I pulled the ticket and called out the number and a woman I never met before jumped up from her seat and let out a little squeal.

After I finished the raffle the band started to sing. I stood still as I heard the familiar lyrics of my wedding dance song. A tear threatened to fall down and I started to rush toward the restroom house so no one would see me. Before I could make it, Samatha jumped in front of me and shoved something into my hand.

"I cannot take any more children today," she said, before storming off.

A tear slid down my cheek and I pressed the back of my hand to my face to cover it up and continued toward the restroom.

When I arrived, I rushed into one of the stalls, ignoring the old stench of urine, and sat down on the seat before letting the tears fall. My shoulders shook like an overloaded wash machine. I tried to cover my mouth but realized there was something in my hand.

I looked down at the contents and it was a lighter and a pack of cigarettes.

***

I looked both ways outside the restroom concession to make sure the area was deserted before bringing the cigarette up to my lips. I took one long pull before I exhaled and I felt myself about to cough. It's been years since I had a smoke and I still was not good at it.

What am I doing,

I thought guilty. I was about to put the stick out when a young male emerged from the men's restroom, his eyes suddenly met mine.

Oh great, just what I needed,

I thought.

"I wasn't...this isn't mine...I," I stumbled over my words. I did not know why I was explaining myself.

The young man did not say anything for a few moments, he just stared at me in surprise.

I tossed the cigarette into the ashbin and pocketed the lighter.

"You're Courtney's mother right," he finally asked, breaking the awkward silence.

"Yes, you must be an old classmate," I said, feeling my shoulders relax.

He continued staring at me, his eyes darkening.

"You..um, you have something..." he stepped closer to me, reaching out, his hand was blazing hot as it brushed against my skin. He pulled a piece of flint from my strap and held it up.