GILF for the Holidays

Summary: 18-year-old helps a GILF and gets a special Christmas present.

Note 1: This is a Holiday 2024 Contest Story so please vote.

Note 2: Thanks to StillStunned, Ohdave1 and Shuj for editing this story.

GILF for the Holidays

"Derek, are you busy right now?" Mom asked as she walked into my room in the basement.

I was playing basketball online, which meant I was. It also meant Mom would think I was too, fortunately. "In the middle of a game," I said.

"How long until you're done?"

"Ten minutes," I said, watching the other team score an easy layup on me.

"Come see me when your game is over."

"Okay." I nodded, taking the ball up the court.

She left.

Me and my anonymous teammate won by three and I headed upstairs a few minutes later.

Mom was decorating Christmas sugar cookies, my favourite.

"I need a favour," she said, without looking up from the delicate work of making a Santa cookie.

"To eat these?" I asked, taking one and biting into it.

"Hey, I just made that!"

"And I just ate it." I shrugged and swallowed the rest. Nothing better than a warm cookie.

"Fine," she sighed, "I made them for you anyways."

"It's why you're the best mom ever."

"Is that the only reason?"

"Well, one of three," I joked.

"You're such a brat."

"So, what did you call me up for?" I asked. "Besides these delicious cookies."

"I need you to go pick up Mrs. Barnes and drive her out to get a Christmas tree," Mom said. "Then take it back to her house and help put it up for her."

"Oh." That was not what I was expecting. Mrs. Barnes lived across the street. She was a sweet old lady in her early sixties, who used to babysit me when I was young.

"With the snowstorm out East, Gwen and Hannah won't be here for at least a couple of days. She's upset about not having a tree up yet."

"Okay." I nodded. "I think I can fit it into my busy schedule."

"Can you go now?"

"After one more of these," I said, snapping up the cookie she'd not even finished decorating.

"Hey!" she called after me as I walked away. "I wasn't done with that!"

I changed out of the shorts that I always wore when Mom was cooking and the house was hot. Instead, I pulled on sweats and a long-sleeved shirt, grabbed my toque, mitts and jacket and headed out.

I drove the truck across the street and went to get Mrs. Barnes. It hit me that she must be pretty lonely living all by herself since her husband died a couple of years ago.

"You are such a sweet boy," she said as I led her to the truck.

"It's the least I can do," I said. "You put up with me in my terrible twos."

"You were a terror," she said with a smile and a soft laugh as I opened the door and assisted her in. She was a bigger woman. I imagined she was a stunner when she was younger, and she was still very pretty even at sixty. Plus, her daughter and granddaughter were absolute knockouts.

I'd had a couple of jerkoff sessions thinking about her granddaughter Hannah, who was a year older than me, and plenty thinking about Gwen - yes, I have a thing for older women. Truth be told, I'd had a few inappropriate fantasies about Mrs. Barnes as well.

"Well, I've kind of grown up," I joked.

"You've turned into a very handsome young man." She was always so sweet.

"Thanks," I smiled, knowing that it wasn't really true. I wasn't very popular at school, and at eighteen I was still a virgin. I mean, I wasn't a troll or anything, but a solid six, outside seven. I'd been working out the past couple of months to balance my academics. "I just have to get the girls at school to think that."

I closed the door, walked around to the driver's side and climbed in. It would be a short ride: the tree lot was only a few minutes away.

As we drove off, she said, "High school girls are brainless if they don't see what a great catch you are."

"Well, I guess they must be pretty dumb." I smiled again.

"Then they don't deserve you," she said, placing her hand on my leg and patting it twice.

"Thanks." I remembered that Mrs. Barnes was always very touchy-feely. "I'm planning to go away to college in the fall. So I don't really want a girlfriend anyways."

"Oh, just a friend with benefits?" she asked.

Caught off guard, I coughed. "Wh-wh-what?" I stammered.

"I'm up with all your teenage lingo," she said. "I was young once, too, and had one or two friends with benefits of my own."

I'd barely managed to get my previous coughing fit under control, and now this! "Mrs. Barnes!" I said when I could breathe again. Still, I managed to inject a playful tone. Her words surprised me, and yet they intrigued me as well.

"Call me Mary. 'Mrs. Barnes' makes me feel a hundred years old."

"Okay," I agreed. "Mary it is.".

"Also," she continued with a slight sigh, "I might not look like it now, but I was quite a looker in my time."

"You're still very pretty, Mrs. Barnes - I mean Mary." I meant it. She had a great smile and intoxicating blue eyes, and her full body showcased all her curves even at sixty.

Not that I was about to let her know I'd had a few jerk-off sessions about her full-figured body. I mean, I only watched MILF porn, and occasionally GILF porn, and I liked a woman with some meat on her bones. I couldn't stand the anorexic look of so many of my classmates.

"You're sweet, but I'm nothing like I used to be," she said with what sounded like a sigh of reminiscence.

"Mary, you're a beautiful woman," I said as we rolled up to a red light. "And your body is healthy and one of a good life lived."

"Oh, Derek, that is the sweetest way to describe me. You really are a sweet boy." She smiled, again resting her hand on my leg. This time she gave it a squeeze and a brief caress before removing it.

I was sure it was just her being sweet. Like I said, she'd always been a touchy-feely woman, like the hug she'd given me a few minutes earlier at her front door. Even so, the brief caress woke up my dick. It was rare that I was ever touched by any girl or woman I wasn't related to.

"I mean it," I said, hoping for more sweet acknowledgement. No matter how innocent, it would likely fuel my late-night self-pleasuring. "You have a woman's body, not like most of my skinny classmates."

"I was once a skinny classmate," she said as the light changed and I started driving again.

"I imagine you were just as beautiful then as you are now." I was doing my best to make her feel better while subtly trying to adjust my dick.

I was beginning to see Mary as a GILF. She was even wearing pantyhose, I realised, letting my eyes drop to the mocha nylons that covered her legs. Pantyhose were my fetish, though I had no idea why. I just found them sexy, and while almost no one my age wore them, many older women did - especially GILFs. So many GILF videos included nylons.

Apparently my attempts to adjust my now hard dick weren't quite as subtle as I hoped because Mrs. Barnes looked right at what I was doing. Her eyes widened a little, but she didn't say anything.

After a brief silence, she said, "I was a cheerleader, prom queen and all that high school drama."

"That makes you the first cheerleader I've ever had in my car," I joked.

She laughed just as we reached the tree lot.

I helped her out and put my arm around her waist to steady her on the uneven terrain. Snow began to fall during the twenty minutes we spent looking at trees. Once she'd picked one, I helped her back to the truck and got one of the workers there to assist me in loading the tree.

On the drive back, Mrs. Barnes said, "Thank you so much, Derek. You're such a gentleman." Again she placed her hand on my leg and gave it a squeeze. This time, she added a slightly longer caress.

"You're welcome," I said as she moved her hand away again, "I'll do anything for you, Mary."

"That's so kind of you.".

"I mean it," I said, trying to find the right words that would get her hand back on my leg. I was surprised by how good it felt, how much it turned me on.

Still, I was eighteen. A virgin. Kissed two girls. Went down on one. Had one hand job. It was only logical that such simple, probably innocent, touches excited me.

"Well," she replied, "I could use some help putting the tree up and decorating it, if you have the time."

"I'm free all day." Mom had already instructed me to help her anyway.

"You're just so sweet!" Her hand returned to my leg, this time just moving up and down for a few delightful seconds before she patted me and withdrew it again. "It will be nice to have some company. I've been quite lonely without Jack."

"I'm so sorry about his passing. He was a great man," I said, and I meant it.

"Yes, he was a wonderful husband and father," she said with a nod, and an air of sadness filled the truck.

"So, when are Gwen and Hannah coming home?" I asked to break the uncomfortable silence.

"In a couple of days, if the storm lets up," she said. "Although who knows, really? It's quite the storm."

"Yeah, they're calling it the storm of the century." I'd watched the news and seen over four feet get dumped on the Eastern states.

"I hope they can get here in time."

"I'm sure they will," I replied, trying to sound reassuring. Then, sure that Mom and Dad would be fine with the offer, I added, "And otherwise you can definitely spend Christmas at our house."

"You really are a sweet young man," she said again, and her hand once more went to my leg for a slightly longer tender caress before withdrawing. "It's really a shame no young lady has scooped you up yet."

"No, it's you who is sweet," I said, fighting the temptation to move my own hand to her leg.

"I mean it," she said. "You're a very handsome young man."

Once again her hand went to my leg, and this time it lingered. "You deserve a woman who knows how to take care of you."

"That's the dream," I joked as she gave my leg a firm squeeze before moving away again.

My dick was raging in my pants and I again had to adjust it. This time I was sure Mrs. Barnes noticed, and smiled.

Unfortunately, we reached her house then and it was the end of the surreal... flirtation? Was Mrs. Barnes flirting with me? I mean, I knew I had trouble reading girls, but I was sure there was something going on here... Yet I was equally sure I was misconstruing this.

She was over sixty years old, after all. I was eighteen.

So I helped her out of the truck, offered her my arm and led her into her home.

Once she was safely inside, I went and grabbed the tree and brought it indoors. Mrs. Barnes already had a tree stand out so all I had to do was put the tree in place.

"Thank you so much," she said as she looked at me and the tree.

"You're welcome," I said, glancing back at her. Now I really got a great look at her not dressed in winter attire. She was only maybe five foot four. She had very large breasts and thick hips, both things I liked in a woman. She'd taken off her boots, and through the beige nylons I saw to my surprise that her toenails were painted red. The splash of colour added to the sexiness of her feet, which were small and delicate. Somehow I'd never imagined her painting her nails. Looking at them now, though, I felt my dick hardening yet again after the brief reprieve while I set up the tree.

"What do I owe you?" she asked.

"Nothing," I replied, looking into her blue eyes.

"That's silly. Your time is worth something."

"I'm serious," I told her, "I'm having fun spending time with you."

"Really?" She was clearly surprised by my words.

"Yes, really," I said, noticing her vulnerable expression, the grey in her long black hair that somehow added to her faded beauty. "So, where are the ornaments and lights?"

"In the basement."

"Show me where and I'll bring them up and help you decorate." I glanced down again at her adorable cute manicured pantyhose-clad toes.

She led me down to the basement and pointed out the boxes. I grabbed the first and made two more trips. By the time I was done, she'd already started to decorate the tree.

Putting the last box down I asked, "What can I do?"

"Can you help me wrap the lights around the tree please?"

For the next thirty minutes or so we decorated the tree. Mrs. Barnes put on some Christmas music, and we sang along to classic tunes.

When we were done she said, "Wait here," and headed into the kitchen.

She came back a few minutes later with cookies and hot chocolate. We sat down, she on the couch and me in an armchair opposite her, and she put her stocking-clad feet up on the coffee table.

Sitting across from her, I sipped on the hot chocolate and admired her silky soles all the time. Just like I couldn't explain my fascination with nylon-clad legs and silky sheer toes, I was also attracted to the silky soles of a woman's foot - yet somehow a woman's bare soles did absolutely nothing for me. I know, I'm a weirdo.

After a few moments of silence, she said, "I'm so thankful for your help."

"No problem," I replied, dragging my eyes away from her soles, "it was fun."

"It's been pleasant to have company," she said, moving one foot over the other.

"Well, I can't lie. It was a nice break from playing video games. I need to get out more."

"Me too," she sighed. "I don't get out nearly as much as I should."

"Me neither," I said, "I mean, when I'm not at school."

"So you really don't have a girlfriend?"

"No." I said, then added, "I've never really liked girls my age." I thought I'd at least try to plant the seed, even if I was sure it wouldn't go anywhere.

"Oh, no?" She wiggled her toes as if she could sense my distraction.

"I mean, I don't have any real experience with women of any age," I admitted, "but girls my age don't do much for me."

"You're not gay, are you?"

"No, no, no," I quickly stressed. "I like girls. I mean women."

"Women?" She readjusted her feet, putting one on top of the other and then changing them back.

"Well, I'm just attracted to older women."

"That's interesting," she murmured.

"I just find girls my age shallow and immature." It was the truth. Sure, I'd love to get a blow job or get to fuck one of the cheerleaders, but usually I masturbated to the teachers.

"I see," she said, seeming to ponder my words.

"Yeah, and truth be told, I am attracted to a woman who isn't going to blow away on a windy day," I added.

"Well, it would take a tornado to move me," she joked.

"Mary, you are an absolutely beautiful woman," I repeated. I realized I'd keep repeating it until she believed it herself.

"You're too kind," she said, rising. "Wait here. I have something to show you."

I adjusted my hard dick before she returned with a photo album in her hands. "Come sit beside me," she said, sitting back down on the couch.

"Okay," I said, getting up and joining her.

"This is me in high school," she explained, flipping open to a page of her in a cheerleader outfit.

"Wow!" She looked absolutely gorgeous.

"I know," she said, "I used to be quite the looker."

"Mary, that's enough." Her nylon-clad knee had been revealed as her dress rode up when she sat, and I placed my hand on it. "You're still a beautiful woman."

"Except twice the size." She didn't move my hand off of her leg.

"And just as beautiful."

"Do you really think so?" She looked completely vulnerable.

"Yes," I replied, my hand still on her leg. "You've aged gracefully."

"It's been a long time since I got a compliment," she whispered, her cheeks a little red.

"Well, here are some more," I said. "You have amazing blue eyes a man could drown in."

"Thanks."

"You have a beautiful full-figured body," I continued.

"Well, it's full-figured." She laughed awkwardly.

"And beautiful," I stressed, giving her knee a soft squeeze. "Plus, unlike girls today you wear nylons, which I have to confess make your legs and feet look super sexy."

"I thought I noticed you admiring my feet."

"If you were my woman I'd worship them," I said, my naughty fantasies leading the way.

"And what would worshipping my feet entail?"

I looked up, surprised at how far I'd dared to go. "Sorry, sorry!" I apologized, "I've been way too forward."

"No." She closed the photo album and placed it beside her. "Perhaps I haven't been forward enough."

She turned her body and swung her legs onto my lap. "Would you be a dear and massage my feet? They're a little sore."

"Sure," I breathed. Her nylon-clad heels were resting right on my hard dick as I moved my hands to her feet.

"Thank you," she said, letting out the softest of moans. "Jack used to always massage my feet."

"He was a lucky man," I said.

"Lucky?"

"Yes," I said, enjoying the soft silky sensation having wondered many times what feeling a woman's legs and feet in nylons would feel like. "Every woman deserves to be catered to."

"You're going to make some woman very happy," she smiled.

"Maybe one day."

"Trust me, once you get out of high school and the cesspool it is and join the real world, you'll be a great catch."

"I look forward to such a time," I said. I mean, I was an average-looking guy. Not ugly, not hot; not skinny and not fat. I just didn't fit into the cliques of popularity. I was too smart to be cool at a school that celebrated football championships, not academic bowls.

"You're going to turn into a handsome man," she continued.

"Thanks." I was flattered, but her words made me a little uncomfortable. I wasn't used to compliments.

"I mean it," she went on. "If I was forty years younger, I'd be all over you."

I laughed awkwardly and moved my hands to her toes, massaging each one individually. Finally, I replied, "And if I was a little older, I'd be all over you."

"Would you now?" she murmured.

"In a heartbeat," I said firmly as I finished her fifth toe on her right foot.

"Why?" She clearly meant it.

"You're a real woman, a beautiful woman." I switched to her other foot and began massaging her sole.

"How so?" She seemed to have forgotten the compliments I'd given her earlier.

"I don't want to objectify you," I protested.

"Please do. I haven't been objectified in a long, long, long time."

I laughed. "Truth?"

"Yes."

"Well, besides your intoxicating eyes that I already mentioned, and the fact you wear nylons, which are my fetish," I began, but halted as she bent her knee and moved her other foot to rest directly on my dick. Maybe it was on purpose, maybe by accident. Either way, it was distracting.

"Go on," she said in a slightly sensual tone.

Her entire sole was resting on my dick. I let my dick twitch against it. If she noticed, her face betrayed no reaction.

I swallowed and went on. "You have very pretty toes, and they're perfectly manicured." I glanced down at the foot resting on my aching dick.

"These toes?" She asked, wiggling them.

"Yes." I let out a small groan as her wiggle caused a slight wave movement along my cock.

"I painted them just yesterday, for the first time in months."

"Well, trust me, they look amazing!" I meant it. "Especially with this shade of nylon."

"I'm flattered," she said, and then asked, "Anything else?"

"You sure? I really don't want to offend you."

"I need this, Derek." Her tone made it clear she did.

Well, if that was what she wanted, I was very willing to give her all the compliments I could. "You have voluptuous breasts, wide sexy hips, and an amazing ass," I rattled off quickly before I could change my mind.

"Derek," she said, moving her foot slightly on my raging rod, "you have no idea how much I needed to hear those words."

"And I meant every word." I moved my hands to her toes. "You're a beautiful woman inside and out."

"You sure you don't have a harem of women wanting you?"

I laughed, and then not even sure why, I muttered, "I've never had sex."