Unwrapping His Package on Christmas Eve

Winter Holidays Story Contest 2023

If you're porn horny, this isn't the story for you. This story is a slow burn. Warning for those with delicate sensibilities- This story contains- older people (mid-fifties), curvy women, big truck/little dick jokes, cats, and a dog. You a fat shamer? Move along—nothing to see here.

For those of you who like a plot along with the sex, continue. I don't think you'll be disappointed in the heat. 😉 As always, emails & comments are welcome. Enjoy! xo DG

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STEVE

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As the dark-tinted window slowly lowered, her mouth moved, breath puffing tiny clouds in the cold morning air. But all I could hear was Jagger shouting, "But it's all right now, in fact, it's a gas.

But it's all right, I'm Jumpin' Jack Flash."

I pointed to my ear and gestured.

She stared at me for a moment, winced, and shut her car off. "Sorry!"

"I was waiting for Leo?" She was like no Leo I'd ever known. She was probably close to my age, mid-fifties. Trendy style on her mostly silver hair. She was buttoning her coat and wrapping a colorful scarf around her neck.

"Happy Christmas Eve!" She extended her hand enthusiastically and said, "I'm Leo. My parents have a great sense of humor and named me Leonora." She flung her arms out wide in an exaggerated gesture. "Clearly, I'm no Leonora!"

When she laughed, it was a genuine belly laugh full of joy. She wasn't self-conscious, throwing her head back and letting the hearty laughter spill out uninhibited. Already, I appreciated her openness and lack of pretense.

"Clearly, you are no Leonora!" I agreed with a chuckle. "And a very merry Christmas Eve to you, too. I'm Steve." I glanced down at the massive red bloodhound sprawled lazily on the floor, her chin resting on my feet. Even after snoozing for the past three hours during our long drive, she had immediately plopped down for a nap as soon as she finished her business in the corner of the mostly empty back parking lot of the Cracker Barrel off Interstate 75. It was a popular meeting spot for transporters like us. "And this is Snickerdoodle." Hearing her name, the wrinkled skin above the bloodhound's eyes crinkled with happiness at our presence, expressing her joy in that unique bloodhound way.

"Snickerdoodle?" Leo giggled. "Well, I guess that fits since you're a girl. Whatever they call you, you will make someone very happy because you're a special Christmas present!" She reached down to pat the dog's head affectionately.

I handed Leo the end of the lead. "Just to warn you, she'll go where she wants to go."

She laughed. "Thanks, I'll be prepared!"

On cue, Snickerdoodle decided to head over to a grassy area, pulling Leo behind her. That dog could move fast when she wanted to.

"Whoa, you're right!"

Leo and I were transporters who had volunteered to get the dog from the shelter in Kentucky to the family that wanted to adopt her in Jamestown, New York. I lived nearby in a suburb of Cincinnati but backtracked into Kentucky to pick Snickerdoodle up because there were no other volunteers. Leo would take the next and last leg on into Jamestown. Usually, our transports were broken into shorter distances, but understandably, few didn't want to volunteer on Christmas Eve.

I couldn't not volunteer to deliver a Christmas present. Not to mention all that coal and stocking stuff.

Snickerdoodle was snuffling along the grassy area between the curbs, pulling Leo behind her, who had the leash wrapped twice around her hand.

"Hey, I'm free today. How about we deliver Snickerdoodle together?" I blurted out, a bit surprised at my own forwardness. But I went with it. "She can be a lot to handle for one person. It'd give us a chance to get to know each other better," I said with a flirtatious grin, emboldened by her surprised but warm smile.

I couldn't take my eyes off her. There was just something magnetic about this woman I had only just met. Throwing caution to the wind, I took a step closer and gently brushed a strand of hair from her face, letting my fingers linger. "What do you say? It could be an adventure. We could get to know each other." My heart raced as I awaited her response, wondering if I was too presumptuous but unable to stop pursuing her.

I saw nothing but relief on her face as the dog pulled her away. "I'd love that, thank you! Yes, to it all! But you'll have a longer drive back to Kentucky?"

I shrugged. "I don't live far from here. No one was picking up the first leg of Snickerdoodle's transport, so I doubled back."

"Oh, okay, I live nearby as well. Wow, aren't you nice to do that!" She smiled, flashing dimples. ​In the cold sky, her eyes, silver-blue like the clouds, radiated a warmth sucking me right in. And it had been some time for that kind of vibe for me.

"I can be. Very," I teased. "We'll take the truck. Your SUV will be fine here for the day." Besides, it's bright lime green. Anyone who'd steal it would be nuts because they wouldn't get too far with that beacon.

I got Snickerdoodle settled into the back seat.

"Okay! Just let me get a few things I don't want to leave in my car."

Leo popped the back hatch of her SUV and leaned in. Forcing my gaze from her perfect ass, I caught a glimpse of a tidy interior with a cozy plaid woven blanket in the backseat. She pulled out a faded green duffel bag that looked packed full. It landed with a heavy thump. Next came two large red shopping bags of Christmas gifts wrapped in shiny paper and giant bows. Leo gently placed them down before grabbing another overstuffed tote, this one with colorful yarn cascading over the sides.

"Sorry for all the stuff. I was prepared for time with my Christmas Eve friends tonight," she explained, a little flustered, looking at the pile on the ground. Her breath came out in small white puffs as she dragged the bags over. I chuckled, picturing her dutifully loading the car with her creations. Just thinking about that made me smile.

I heaved the heavy duffel into the cab as Leo tried corralling all the rolling balls of yarn back into the tote. "I've got the rest," I assured her. Soon enough, we were packed up and ready to head out.

By the time we left, as requested, all her belongings were piled at her feet, her jacket neatly folded on top.

We buckled in and were on our way. Leo was fashionable but still practical. The black knee-high boots were high but thick-heeled and appropriate for snow. Black tights and a short skirt cuddled her ass. A silvery blue scarf that matched her eyes twisted like a necklace on her black cowl neck. I squirmed a little in my seat at my dick that was making way too much of this.

She must have sensed that I had checked out her attire because she said, "I must look a little dressed up to drive a dog across the state, huh?" she laughed, and I grinned. "I had some business to take care of at a gallery right down the road."

"You look beautiful, Leo." I wasn't surprised by her colorful, but not flashy, fashion. "Gallery? You're an artist?"

"I am. I'm a textile artist. I work with fiber instead of paint." She leaned over to crank the song up. "Oh! I love this song!"

She vibed Jagger but seemed to be happy with the traditional Christmas songs that were on my radio. I'm not sure what that says about either of us. Although out of season, I listened to the Stones, Led Zeppelin, and all, I wasn't such a boring guy.

"What more can I do," she had a beautiful voice, "Baby, all I want for Christmas is youuuu," she sang with the whole shoulder and hand action going.

And all I want for Christmas is you.

I glanced over and smiled, "You have a great voice."

"Oh my gosh, I'm sorry, I just took over your radio," she apologized, leaning forward and reaching to lower the sound.

I couldn't help but notice she filled out that sweater very, very nicely. I've always been a T&A man and noticed these things. Never too old for that. This was a woman you could take out to dinner who would order a meal instead of picking at a salad. I liked that—a lot.

"Make yourself at home!" Oddly enough, it made me happy that she felt so comfortable with me.

She waved her hand. "This is sort of like a living room in here."

"I spent so much time in the truck. I wanted to get as much comfort as I could."

"Yeah, it is a big truck. You know what they say about men who drive big trucks," she giggled and clapped a hand over her mouth. "What do you do?" she asked, saving herself, but I was biting back a grin.

If I have my way, you'll learn about that big truck/little dick myth someday.

I cleared my throat, getting past my vision of her in my bed. "I'm a welder. Well, actually a retired welder now."

"You're too young, so you must not have retired too long ago?"

"Why thank you, and you're right. Less than a year. I was happy to be able to do it at fifty-five. I'd invested and did all the right things to get out early."

"Like, work your ass off."

I laughed. "You got that right! Although I do love to weld and still pick up a few side jobs."

"I can see that. If you're doing something you love, it's really not a job. I'm fortunate that, for the most part, I can set my own hours. My studio is at home." She was quiet for a moment. "I'm not sure I'd ever really quit doing what I do. Not sure what I'd do with myself," she laughed.

"Are you married?" I was finally able to slide in that oh-so-important question.

"No, never have. I was so busy building my career. Then, when I became successful," Leo air quoted, rolling her eyes, "I began to travel and had no time to breathe, much less for relationships."

"Oh, so you travel a lot?" I tried to hide the disappointment in my voice.

"Not so much anymore. I hold week-long workshops several times a year, and they travel to me now," she chuckled. "It was stressful for a while. I could have scheduled workshops every weekend all over the country, and too often did. I just had to make sure I had time for travel between, and still, I often cut it close."

"Good for you, Leo. You recognized when you made it and took advantage as you should have." I looked at Leo in yet another light. "You certainly are successful."

She smoothed a hand over her skirt. It was mid-thigh, but her black tights kept everything respectable. "I'm home more now, yeah. My cat loves it," she laughed.

"You have a cat? So, do I? Dogs are too needy for me. Zeus is my house panther. Always happy to see me when I get home and content to lie on my shoulder or lap. She takes care of her own business and eats when she wants. She doesn't need me around to do that."

"My girl is a grey floof named Alberta."

We both laughed when we heard a loud snuffle from the backseat.

"I wonder if that was his opinion of the cat's name," she laughed. "Snickerdoodle is a good doggo," she said, looking back. "She's content to just lay on your seat."

"I thought we'd stop in Columbus, get a bite to eat, and get her out for a walk."

"Sounds good to me. I can go for a coffee at least." She wiggled back into the seat and crossed her legs on the seat, and I stifled a groan at her flexibility. "This is really comfortable."

I pointed out the heat controls for her side of the truck and the seat options. We rode in comfortable silence until we found an exit with an arms-length list of restaurants on the highway food sign.

"I'll get Snickerdoodle some water and food if you want to go in and order?"

"Perfect!" She bundled up again and, refusing any money, made her way to the restaurant.

Leo was hesitant about eating in the truck, but I flipped up the table between us that had flat space for food and several size cup holders.

"Whoa, fancy!" She emptied the bags of food and opened the steaming coffees. "I wasn't sure how you liked your burgers, so I got it with everything. You can pick off what you don't want."

I laughed because that was precisely what I'd have done, but I saw the flush on her cheeks.

"I'm not laughing at you... I am, but only because that's what I'd have done. Pick off what you don't want."

"Oh! Okay," she giggled, twirling a French fry in ketchup, then sucking it off before she ate it, then flicking her tongue across her lips for any errant condiment.

Not even two hours into the trip, I was already fighting the urge to pull Leo into my lap and kiss her sweet lips. Everything about her excited me more and more. The way she gestured excitedly, her unabashed singing, her thoughtful questions, her eyes shining with curiosity and life. She was just so full of life, pulling me right in.

I'd found that most women my age seemed to fixate too much on trying to fight the aging process. Obsessing over wrinkles, spots, and every new pound that crept on. Fussing to cover the gray hairs and perfect their outfit before being seen in public.

Don't get me wrong, I understand society's pressure on women to look flawless. But there was something so special about a woman who could embrace growing older gracefully. Who carried herself with quiet confidence rather than vanity.

Leo was like a breath of fresh air. She didn't seem hung up on her looks or trying to impress anyone. Whether chatting over coffee or bundled up in the blizzard, she had a natural, effortless beauty about her. And no hair dye, my particular nit. Old ladies that dye their hair red or blonde... They look ridiculous because they cannot pull it off as natural.

Some might call her eccentric with her artsy style and quirky habits. But I found it charming. Leo was comfortable just being herself. Her smile lit up a room more than any fancy outfit or dye job could hope to.

Now, that's what I call truly beautiful - a woman with the wisdom to know her worth comes from within. Who realizes laugh lines and gray hairs tell the story of a life well-lived. If only more ladies realized that embracing who they are is more appealing than fighting nature. Leo was a reminder that the right man will see past the surface and fall for what's underneath.

I gripped the steering wheel tight, trying to focus on the road ahead. But my mind kept drifting to Leo, sitting just a few feet away. I wondered what her head would be like resting on my shoulder if she tasted like the peppermint candy cane she'd been nibbling on. I shook myself out of those daydreams.

The last thing I wanted to do was make Leo uncomfortable. She was just being friendly, not looking for romance with an old gearhead like me. But there was no denying that I was drawn to everything about that woman: her passion, smile, and zest for living. I can't remember the last time I felt this spark. If ever.

"Still got a few hours to go." I sucked in a deep breath and cranked up the radio, needing a distraction. Oh man, this will be a long, torturous drive. I could only hope my self-control would last.

Leo nodded cheerfully, humming the Christmas tunes and sucking on the candy cane.

I wondered when the last time I reacted like to any woman. After my divorce fifteen years ago, I got busy with work and didn't meet many women I wanted to go out with. Although I'm sure if I'd met Leo, she would have stopped me in my tracks.

My divorce was amicable. We were just bored with each other. I couldn't imagine my life with her, nor she, me. We were young and didn't realize how long forever really was.

"Do you mind if I use this?" she asked, tapping the table.

"No, of course not." She riffled through all the bags stacked around her legs until she pulled up the bag with the yarn. "You can put some of those bags in the back, so you have more room. I don't think Snickerdoodle would take the energy to get into them," I laughed.

"He might because he'd smell the food."

"Food?"

"Well, not food exactly," she said, stringing yarn across the seat. "I have Christmas presents with chocolate."

"Ahhhh, that might not be a great idea then. You're going to your family for the holiday?"

Leo paused, seeming to choose her words carefully. "Well, I was an only child. And my parents passed some years back." She spoke matter-of-factly, but I sensed a quiet sadness in her tone.

"I've got a close group of women, all around fifty-something, in the same boat. No family of our own. We make sure none of us are alone on the holidays. We'll stay up late on Christmas Eve, exchange gifts, talk, and laugh. Like a silver girl's slumber party," she laughed.

I nodded, picturing her surrounded by friends, making their own fun. "That's really thoughtful of you all," I said.

Leo just shrugged, keeping her eyes on the needlework in her lap. "It's nice to have companionship."

After a few moments, she glanced my way. "What about you? What were your plans for tomorrow?" She bit her lip apologetically. "Before I ruined your Christmas Eve, that is."

I waved off her concern. "Shoot, I didn't have any real plans tonight." I paused, debating how much to share. "My folks passed years ago, and my brother lives in California. We keep in touch but rarely see each other."

It was the truth, though I couldn't yet let on how much more she meant to me already. I hoped someday I could be the one keeping her company on Christmas. For now, I'd cherish every moment fate had brought us together.

I rubbed my jaw, the stubble rasping under my fingers. "Few years back, my buddy at the shop told me about a free Christmas dinner for veterans. I volunteered to cook, clean, and do whatever they needed. Some who show up actually have means, but I think they're just starved for company."

Leo stopped knitting, her eyes warm with interest. I cleared my throat, feeling a bit self-conscious. "I know it's not much, but I've got a handful of fellas who come back each year who I look forward to seeing." I chuckled, picturing their weathered faces. "They're quite the characters. Swapping stories and jokes over turkey and stuffing makes my day as much as theirs, I bet."

I snuck a glance at Leo. She set down her project ultimately, giving me her full attention. "That's really kind of you, Steve," she said softly. "I'm sure you've made a lot of folks very happy on Christmas."

Her genuine praise made me duck my head. I couldn't remember when a woman looked at me with such respect. For a second, I let myself pretend I was the catch she seemed to think I was.

The clouds continued to get more ominous the further north we were in Ohio. I kept moving, hoping we'd get our Christmas package delivered and back southbound before heavy snow hit.

I heard the rasp of the zipper on Leo's duffel bag as she rooted around. We were on a stretch of road with little traffic, so I was able to check her out. Zippers on each boot hummed down.

Suddenly, she lifted her leg, her foot nearly on the dash, and slipped on a little slipper with a cat face. By the time she lifted the other leg, I was squirming in my seat, trying to get comfortable because my jeans got tight.

She glanced over at me. Her skirt hiked further up her thigh—but those damn tights. I smiled with gritted teeth, and she giggled. "Just getting comfortable."

I'll get you comfortable, all right, I thought.

But I just nodded.

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LEONORA dba LEO

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I'll admit I was really feeling myself on the drive over. With the Rolling Stones blasting, I was rocking out and daydreaming about the gallery opening. Visions of potential buyers admiring my weavings danced through my head.

When I pulled up and saw Steve waiting there, I was mid-headbang to 'Jumpin' Jack Flash.' I probably looked like a fool, hair flying everywhere as I jammed out. In my excitement, I completely forgot to turn the radio down.