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