Mad About Maddie

Being divorced for 8 years and in my late 40s, I had pretty much taken myself out of the dating pool to instead focus on working to build up extra money. Also to get myself out of the house more. After what seemed like weeks if applying for part time jobs, I landed an easy gig doing deliveries for a pharmacy.

On the first day it didnt take long to realize that I was the oldest person there by a long shot. The closest to me was the early 30s aged pharmacist. All of the pharmacy techs were beautiful women in their mid to late 20s, and the cashier/clerk was a girl named Maddie who was fresh out of high school.

Maddie was an average height girl with a nice figure that she didnt mind showing in skinny jeans and a work polo that fit her snugly. B cup breasts pushed out the chest of her shirtm her long brown hair was to the middle of her back and always in a ponytail. Her hazel eyes were framed by large framed glasses. When she smiled or laughed, her eyes seemed to light up.

When I wasnt on deliveries, I would help stock shelves with Maddie. When it got busy, I would run the second register. Maddie and I quickly developed a friendship. Talking to her was easy, her intelligence was clear in the way she spoke. She tried her best to find out about me personally but I resisted by changing the subject. I preferred cracking little jokes to hear her laugh.

"So, I dont see a ring, so you're not married?"

"Not for 8 years now"

"So you probably go out a lot with all that freedom" her eyes were trying to read my expression

"I work two jobs, no time to go out"

"You know what they say about all work and no play" she grinned

"Yeah, all the bills get paid" I grinned back

"Not where I was going with that. So any kids?"

"They are both grown and live out of state" I couldn't believe she was getting information out of me.

About that time, a customer walked up to the counter with a question. When I turned to greet her, I felt my phone get pulled from my back pocket. Maddie grabbed my hand and pulled my thumb to the unlock sensor. I answered the question and turned to see her typing on my phone

"What are you doing?"

"My number is in the phone, and I found your number. Your kids are moved away, you are all work and no fun. Consider me your new daughter and im gonna teach you how to love again"

"And how do you plan to do that?"

"When I text, you have to come out with me. We will have fun. Tonight when we close, you are coming out for coffee with me"

"I have to work in the morning" I tried to get out of it

"I dont take no for an answer"

I couldn't have told Maddie no even if I wanted to. I gave in to the fact that I was going out after work. Right at closing time, Maddie told me coffee had changed to dinner, since she was hungry. We were two of the last to leave, she was about to head to her car when I stopped her and offered to drive. Being the gentleman I was, I opened the door for her. As I drove, we talked, I started to open up to someone for the first time in almost a decade. She was so much younger so I figured there was no harm in sharing a little more about myself.

Having dinner with someone in a decent restaurant was a nice change of pace from the boring life that I had been living. I soon found out that she was a fan of classic rock like myself, and she was also knowledgeable about cars. How could I have things in common with someone so young. She had learned about me, I decided to ask about her

"So is there a special guy in your life?"

"My last boyfriend was two years ago, he was a douchebag. I have been dating a girl for the last year"

"So that means you're a..."

"No, im not a lesbian, I am bisexual" she cut me off and giggled "guys my age are self centered assholes"

"They usually are until 30"

"So only 12 more years of eating pussy" she said with a grin.

"I forgot what that's like" I said without thinking

"When was the last time you got laid?" Her eyes had a serious look in them

"I wish I could remember. I cant do one night stands, I dont think its very respectful to women. They deserve respect, honesty, and trust"

"Spoken like a true gentleman" she said and leaned forward to take a bite of her foodm when she did, I got a look down her tip enough to see her cleavage. My cock stiffened a little.

When the check came, Maddie offered money. I refused, paying the check myself, Maddie left the tip and I drove her back to her car. Before she got out, she thanked me for dinner and we hugged. I couldn't help but watch her perfect ass in her skinny jeans until she got to her car. Then I drove home, where I couldn't help but masturbate thinking about her.

The next afternoon, I made my way from the day job to the pharmacy, inside i was excited to work with Maddie again, the night before had been so much fun. I made my way to the counter to find out if there were any deliveries, there weren't any. Maddie came out of the break room wearing a knee length pencil skirt that fit her tight and a blouse that was also on the snug side.

"You look very nice" I greeted her

"Thank you, I just felt like a skirt today. I had fun last night"

"I did too, thank you for good conversation"

Shortly after, I was sent on a few rush deliveries. As I drove, my mind kept playing out how good she looked in a skirt. I had not had this many thoughts about a woman in longer than I could remember. Then I had to remind myself that she was only 18. When I returned from my deliveries, I returned to the register area in case it got busy.

"Let's do dinner again tonight" Maddie said

"Okay, anywhere you have in mind?"

"My girlfriend is gone to visit her aunt, come to my place, ill text you the address. I wanna cook for you"

"Someone cooking for me? How could I say no?"

The evening continued with our usual conversation, I was starting to enjoy this job more than my day job thanks to her. After work, I made my way home to wait for her text. Looking at the clock, I knew the next day would be a struggle, so I texted my boss that I needed to use a sick day. Shortly after, Maddie texted an address. I was tired but shook it off at the thought of hanging out with a hot, young girl.

Knocking on her apartment door a short time later, Maddie opened the door and my knees felt weak. Her long brown hair wasnt in a ponytail. She didnt have her glasses on, and her skirt and blouse was replaced by a form fitting mini dress and heels she was a vision of perfection. I greeted her with a hug and followed her inside. Maddie led me into the kitchen. By the windows was a small table with two plates of lasagna and two glasses of wine. From the corner of my eye, I saw a bag half in the trash with a doordash sticker on it

"You know, doordash isn't cooking" I joked

"Yeah it is, I just outsourced the cooking" she said with a smile as she looked over her shoulder

I took a moment to silently admire how good her ass looked in the mini dress. Her legs were flawless, she looked even hotter without her glasses on and her hair down. As we started to eat, I had to remind myself that she had a girlfriend and she was young enough to be my granddaughter.

The conversation flowed as easily as it did at work, she continuously smiled, and frequently pushed her hair back over her ear. She did all the things I remember from back in my dating days.

"I dont know if I told you yet but you look amazing tonight" I said as we finished eating, my hands rested beside by glasses

"Thank you"

"You didnt have to get all dressed up for me"

"Of course I did, it's a special occasion. You haven't been on a date in years, and i haven't been on a date with a man in years"

"You definitely made the occasion special"

"Rick" Maddie laid her hands on mine "I haven't had these feelings in a long time, the moment I saw you I saw a caring man who puts others first. That's the kind of man I need:

"What about your girlfriend?"

"She doesn't have to know, come dance with me" she said and stood. I took one last sip of wine and stood.

Maddie put on slow music on her phone and set it on the table. Her high heels made her almost as tall as me. My arms around her waist, her arms over my shoulders, we swayed to the music, keeping eye contact.

"Maddie, the moment I met you, I met a young, beautiful, sweet, and smart woman. I didnt think a second job would be fun, but you make it fun. You deserve the best"

"You are the best" her face was nearing mine. I braced myself for what was coming when I closed my eyes.

Maddie's soft lips met mine, a series of lingering lip kisses. I had forgotten how good it felt to kiss someone. Our lips parted and her soft tongue gently rubbed mine. I held her tighter, my hands moved down to her ass. When I did, she kissed me harder. After a few minutes of non stop kissing, our lips parted.

"Let's go somewhere more comfortable"

"Are you sure?"

"Very sure" she stepped back and took my hand. She picked up her phone and led me down the hall to the bedroom.

Maddie set her phone on the bedside table, the music was a Playlist of romantic music. On the table was a picture of her and her girlfriend. Maddie laid the picture face down and turned back to me. Her smile was so sweet. Her eyes stayed on mine as she started to unbutton my shirt slowly. When it was fully open, her soft hands glided over my skin. My hand cupped her cheek, my thumb caressing her cheek. Then my hands moved under her arms and up to the zipper. Lowering it all the way to her lower back, my hands moved up her sides and to her breasts that were cupped by a red bra.

As we started to kiss again, Maddie pushed her dress over her hips and let it fall to the floor. Then she stepped out of her high heels. Her hands unbuttoned my pants and I let them fall down my legs. Stepping out of my shoes and kicking off my shoes, we moved onto the bed she shared with her girlfriend. On our sides, facing each other, we kissed more passionately. Maddie pushed against me and rolled onto me. My hands moved to the clasp of her bra and unhooked it. The bra found its new place on the floor, her breasts felt so good against my chest. My hands moved down her back to her back to her bare ass cheeks. My thumbs hooked the waistband of her thong and pushed it down.

Maddie lifted her hips and helped get it off. She slid her hands down to my underwear and helped me take them off. My hard cock now free, Maddie started to kiss down my chest and stomach, closer to my cock.

"Ive missed cock so much" she said as her lips kissed up and down my shaft. Once at the bottom of it, her lips moved to my balls and took them in her mouth as she started to stroke my cock. I let out a moan of pleasure

Her lips moved back up tye shaft, her tongue running around the head, I couldn't believe I was about to have sex with a gorgeous 18 year old girl. Maddie took my cock into her mouth and started to suck it, her mouth glided up and down it, her eyes open and looking up at me. She had no gag reflex as she took all of it in her mouth. Her lace quickened. I moaned happily, the best blow job of my life.

After a few minutes she took it from her mouth and kissed up my body, back in my arms, we resumed kissing as we rolled until she was on her back. My lips made their way down her soft, young body to her breasts. Kissing the mounds I had imagined since we met my lips made their way to her now hard nipples. I heard her start to moan happily as my tongue circled and flicked them.

As I kissed my way down her belly, her fingers ran through my hair, I kissed the bald patch above her pussy and her legs parted wider. I reached her beautiful young pussy and started to lightly lick. Maddie began to moan louder, her moans were the most beautiful sound I had heard in a long time. I took my time exploring her young pussy. Circles with my tongue, up and down strokes. My tongue moved to her opening and started to lick around it.

Maddies fingers moved to her clit as I slid my tongue just inside her. While I licked, she played with her clit. Her moans were now almost screams of pleasure, her fingers flew on her pussy until she came. Her body shaking uncontrollably as her juices flowed. I began to kiss my way back up her body and we resumed kissing.

As we kissed, I moved the tip of my cock to her hole and started to push, she waa so tight that it took me a few tries before the head started to enter. The first pussy I had been in in longer than I could remember. Once I started to pump her pussy slowly it all became a blur of pleasure, our moans grew louder than the music, her smooth perfect legs wrapped around me. I picked up the pace, and before I knew it, Maddie was screaming as she came for a second time. I felt my orgasm building and with a groan, came inside my young coworker.

I stayed on top of her after I pulled out, just looking in each other's eyes, I stroked her cheek with my thumb. Maddie smiled proudly and I saw her eyes tear up

"Are you okay?" I asked

"Yes, im perfect, you're my love at first sight" she said softly

"You're my love at first sight too"

"Spend the night with me"

"I wouldn't want to spend it anywhere else"

Rolling to her side, Maddie laid her head on my chest and I held her as we fell asleep. My last thought was how glad I was that I was taking the next day off from my day job.