In Dreams
This story contains descriptions of close family members engaged in entirely inappropriate activities that some may find either disturbing or hot. If you find family members fantasizing about or taking liberties with each other or otherwise behaving in naughty ways, then you probably should stop reading right about...now.
All characters in this story are fictional and are eighteen years or older. Any resemblance to any real person, living, dead or under the age of eighteen, is in your own dirty little mind. Sadly, most of the events portrayed in this story are not based on true events. I wish.
If you are still reading and are not offended by MILF and believe siblings behaving in very naughty ways is hot, I hope you enjoy this story.
Part 4
I had to travel to Denver for work.
To be honest, I was looking forward to it. A week in a hotel room, freedom from sleeping beside my wife while I dreamed of my sister. A week when I could go to sleep at night alone with my dreams!
Except, my dreams were never alone. My sister shared them with me.
I had the middle seat on the plane, which I hate, but it was booked by corporate, and they were fucking idiots, so they probably did it on purpose. The guy in the window seat looked like a preacher. Pretty sure he was, too. In the aisle seat, a woman stood to let me in, or possible to let me take a good look at her. Strange, because she was probably almost twice my age but still sexy as hell. She must have been something incredible thirty, forty years ago.
Slender and petite, her hair blonde and well-styled with green eyes, this woman was nothing to scoff at now, either. A MILF--very possibly a GILF.
Okay, technically my sister is a MILF, because she has kids despite being like half this woman's age, but the middle-aged hottie sitting down after I squeezed by facing her truly grabbed my attention by the balls. Usually I back in, aiming my ass at the person letting me by, but I wanted to look closely at this sexy old lady. Worked out well, too, because she accidentally bumped me with her boobs as I went past.
Well, might have been an accident.
"Hi, I'm J.C."
"Eleanor," she offered her hand with a smile. I have no idea what the pastor's name is, nor do I care.
"Are you heading for Denver, too?"
"No, just changing planes there, flying on to Oregon."
"That's too bad," I heard myself saying, and realized I was flirting with this gorgeous lady. I should be ashamed of myself, but compared to what I'd been doing over the last few weeks, flirting with a woman old enough to be my mom was nothing at all to be ashamed of. In fact, it was probably the most normal thing I had done in a month.
GILF, I found out soon enough. She was on her way to visit her daughter and grandchildren outside Eugene. She was a widow, which was too bad, particularly since she only had an hour layover in Denver.
"I hope you don't mind, but I always fall asleep on planes," she said. "I don't want you to think I find you boring or something if I nod off soon as we take off."
"Oh, no problem. I may take a nap, too."
After the nights I'd had in the weeks before, I needed some sleep. Almost every night I lay awake thinking of what was to come, so to speak. And soon after I fell asleep, nearly every night I awakened with a wet dream, after which I had trouble getting back to sleep because my brain was on fire.
She gave me a big smile, her brilliant green eyes smiling, as well. "Well, then, we might sleep together."
Holy shit, Grandma Eleanor was flirting with me, too! I started sprouting wood, which was really uncomfortable the way my dick was wedged in my jeans, but I could not figure out a way to extricate it without looking like I was playing with myself after that, so I just wiggled my ass in my seat and tried to let it work itself free as it sprang to life.
Sure enough, they served us our drinks. Eleanor and I both ordered red wine, and before either of us finished it, her eyes were starting to close and I was having trouble keeping mine open, despite the cleavagy blouse Grandma was wearing, which she caught me looking down maybe a hundred times as we chatted over a glass of wine.
The preacher had a Bible open on his lap, so I figure he was praying the plane would crash into a mountain before I jumped this GILF right then and there.
Eleanor fell asleep first, leaning on the armrest between us; I leaned on it, too, so our shoulders were together. Her head tilted a little to the side and she smiled, so I figured we might end up cuddling before landing.
"Do you want me to lift the armrest?"
"Oh, that would be nice," she said, and I am sure the preacher was thinking even dirtier thoughts than either of us were.
Eleanor was asleep on my shoulder in minutes, which was great because now I could move my wood to a comfortable position inside my jeans. I made sure the preacher noticed me do it, too, because it was so fun making him as uncomfortable as possible.
It wasn't like this GILF and I were going to join the Mile High Club while he hit the stewardess button yelling for help, right?
Pretty soon, my cheek was resting on Eleanor's head as she left a little drool on my shoulder. She had a bit more hairspray in that I would have liked, because it made her hair a little stiff to sleep on, but I was so damn sleepy right then...
That in-flight phone in the back of the seat in front of me rang. That was weird--do these phones even take calls?
"Hello?"
"Hi, big brother! Just wanted to wish you a happy flight! Wish I could be there with you."
"You will be there at the hotel, won't you?"
"Wouldn't miss it for the world," she said. "Well, enjoy your flight. I'll be thinking of you!" I said goodbye and hung up the phone and immediately fell back asleep.
What woke me the next time was Alyssa crawling up from the storage space under my seat, emerging kneeling between my knees.
"What are you doing here?"
"What are
you
doing?" Her eyes flickered over to Grandma Eleanor.
"I was sleeping until you woke me up."
Eleanor nuzzled her head against my chest, so I moved a little to enjoy it. My sister was staring at the bulge in my pants. "You seem to like Eleanor."
"What are you doing on this flight? And why are you under my seat? Don't you have your own seat?"
"I am your carry-on baggage. Where did you think I'd be?"
Oh, right. I could not leave my sister behind while I went to Denver. It all made perfect sense, as dreams always do, no matter how wacky they are. My sister started rubbing my thigh, which was just perfect.
"Who is this?"
Eleanor was awake and looking at my sister between my legs. "That's my sister, Alyssa."
"Hi!"
"Hi!"
"Listen, I don't mind if you and my brother... you know."
"No, young lady, I am afraid I don't know what you are talking about."
"Don't they call it the Mile High Club?"
My face turned a bright red, which I could see because sometimes I see myself in my dreams, like I was watching the whole show through the preacher's eyes.
"Oh, are you a member of the Mile High Club, J.C.?"
"Don't listen to my sister--she's just trying to get me in trouble."
"It's okay," Alyssa said, caressing my thighs now with those soft, tiny hands of hers. My cock was forged of iron. "I don't mind if y'all do it. In fact, it will be fun to watch."
"I like your sister, J.C."
"Yeah, me too," I said. "Eleanor, are you awake or asleep?"
"I really don't know."
This was my strangest dream yet, but it had some serious potential. Alyssa was between my legs, motioning toward the GILF with her head and eyes, so I started unbuttoning her blouse because--well, I probably don't need to explain it to you, right?
Eleanor was wearing a sexy black lace bra that would have been naughty on a woman half her age. On her, it was perfect! Her boobs were bigger than my sister's and not as firm, of course, but they were frickin' amazing for a woman of her age. They were pretty darn hot for a woman of any age.
I asked her, "Do you mind?"
"Oh, sorry. I forget where we are," Eleanor said, so she unbuckled her seatbelt and pulled her blouse off.
Everyone else on the flight was watching the movie or sleeping. The only ones enjoying the in-flight entertainment were my sister and I. Well, Eleanor was having a great flight, too, and I had the distinct impression she was really here, in our dream, along with me and my sis.
Damn, that lady can kiss! I really did not expect that, but she kissed with skill and hunger. Meanwhile, my sister reached up between my legs to undo my seatbelt, making sure to rub by bulging jeans for a while as I swapped spit with the GILF in seat C.
This was the hottest dream yet, and the first one I realized was a dream while having it. I was squeezing her big ol' titties and she seemed to like that as much as I did. Before long, she undid her bra and slipped out of it, because it was hard for me to reach and all. My sister undid my pants and I lifted Eleanor's skirt enough to reveal black lace panties matching the bra laying out in the aisle.
That little minx! Those panties were see-though, and through them I could see she had shaved her bush into a white landing strip. Hard to tell through the fabric if her bush was blonde or gray, but it didn't matter--it was sexy either way.
Somehow, my sister wrangled my hard-on out of my boxers, which seemed impossible because the fly seemed far too small for the condition it was in at the time. I was rubbing between Grandma's legs, and her panties were soaked. Her tongue circled mine, slowly and seductively while my sister slowly stroked my rod.
