In Dreams Ch. 04

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.

"Do you want me to lube this up for you?" Alyssa was looking at Eleanor, my cock in her grip.

"Oh, that is so sweet! That will be very nice of you," she answered then turned to me. "Your sister is such a nice girl."

"She sure is."

That nice girl was licking my cock from root to tip, making sure to coat it with a thick layer of saliva for plenty of lube. When finished, her tongue curled slowly away, still attached to my cock by a long string of saliva that grew until she closed her pale pink lips. There it hung, from her lower lip, like some sort of sordid metaphor.

Eleanor climbed on top of me, straddling me, and I pulled her lace panties off and dropped them onto the preacher's Bible. He was asleep with the Bible on his lap, missing the show. She lowered herself onto me, blocking my view of my sister as her snatch slid down the cock lubed with my sister's spit.

I fucking came instantly. Eleanor was still asleep in a puddle of drool on my shoulder, but her eyes flickered open and her body jerked a little, like she got an electric shock.

"Oh! Oh, my! I must have--goodness, what a dream!"

Holy. Fucking. Shit! This was contagious! Now this GILF was sharing our dream, having her own orgasm, too, no doubt. I was still coming, and it felt like someone had dumped a large jar of honey down my pants. A few more squirts came out, leaving me panting. Eleanor smiled, then waved her open hand over her face as a fan.

"Sorry about your shirt," she said, and I saw the drool and a smear of red lipstick and was glad I was not flying home for my wife to meet me at the airport. She smiled and blushed, then looked down at my bulging jeans. "Oh, dear!"

I glanced down at my lap to see an enormous cumstain soaking through my jeans.

If we had been in an exit aisle, I would have pulled that hatch open and jumped right out of that airplane. Creaming my jeans while cuddling with a grandmother I never met before on an airplane was easily the most embarrassing thing I had ever done.

"Looks like you had the same kind of dream I had." And she smiled sweetly, knowingly, trying to make me feel better about blowing my wad in my pants in public. She had that airline blanket draped over her knees, so she lifted it onto my lap, spreading it out and then, for good measure, lightly patted the bulge, still visible under the blanket

She whispered, "I'll go get you some tissue. Maybe it will help." Then she patted my hand, gave my cheek a little kiss, and went to the bathroom in the rear.

My freaking head was spinning. I was seriously digging this sexy little granny, and if she was not flying out, would totally ask her back to my room and bang her brains out--for real, this time.

But it had been real. And, was Alyssa really in on it? Had we really just had a threesome? And been christened into the Mile High Club, to boot?

Eleanor and I deplaned our flight together. Her connecting flight was to the left, the exit to the right, so I said, "Looks like this is goodbye."

"It was a very good flight, wasn't it?"

"It was a pleasure meeting you," I said, completely meaning it and wondering if she understood.

"Same here," she said, eyes dropping down to my crotch. "See? Dried out just as I said it would."

"Yes, you did." She was not in a hurry to leave, which was fine with me. Despite her age, she was a joy to look at--even with her clothes on.

"Well, goodbye then," she said. Before I could respond, she attacked me, planting a massive, wet kiss on me, lips wide open and her tongue deep in my mouth. I pulled her close and thought, what the hell, and grabbed her ass like we were a couple of teenagers. We stood there for the longest time, Frenching and me groping her cute little ass, until she finally pulled away and walked off, turning around once to let me have a final look at those gorgeous green eyes.

Well, maybe not final. I did ask for her phone number, and she gave it to me, so who knows?

Ten seconds after I checked into my hotel, I was on Skype with my sister. She was at work, so she went out into the courtyard outside her office building to call me back.

"How was your flight?" She had that totally sexy, wicked grin on her face that looks so hot.

"What do you know about it?"

"Oh, maybe a thing or two."

"But you're at work."

"Yeah, funny thing about that. I haven't been getting much sleep lately--I wonder why?--so I went out to my car in the parking garage and took a little nap. Can you guess what I dreamed about?"

"Tell me."

"Your seatmate, Eleanor? She is cute as a button, isn't she? I never would have pegged her as your type, but I guess I don't know my big brother as well as I thought I did."

"Okay, can I ask you a strange question?"

"After everything we've asked of each other for the last month, you have to ask?"

"Did you call me? On that SkyPhone thing?"

"I didn't know you could do that."

"Yeah, me neither."

"So, is this your room?"

"Sure is." I panned the phone so she could take it all in.

"Well, try to stay awake for a few more hours. Then, how 'bout I drop by for a little visit?"

We Skyped for at least an hour after dinner. She was two hours ahead, so it was getting late there, and she was starting to yawn. I didn't want to ring off, even though I knew she was going to come by in person soon. Or, in spirit or whatever it was that happens when we sleep.

When we did hang up, I went to take a shower because my pubes were crusty with dried spunk, and I really didn't want my sister to see that.

I drank the bottle of wine I stopped to pick up on the way here and decided to surprise Alyssa when she showed up. In bed and buzzed with wine, I drifted off quickly to sleep.

Almost immediately, my sister lifted up the covers and slid in underneath with me. Wearing a long, white silk nightgown, it made her look like a bride on her wedding night. It fit her perfectly; loose enough to flow when she moved, tight enough to show off every curve and delight of her lovely body.

"Finally, we are on our own little vacation," she said, reaching for me, her hand finding my hip. "Are you naked?"

"Do you like me naked?"

"Have I ever seen you naked?"

Her hands were all over me, as mine were on her. This was not like our other dreams, but felt real, like he had literally walked into my Denver hotel and climbed into bed with me, and I started to wonder if I was asleep at all.

But we were asleep, and we weren't in Denver at all, as I soon saw. The curtains opened to reveal a tropical beach with palm trees. And her nightgown was red. Her body feels so lovely through silk!

"Did you save any strength after that flight?"

"Did you do that?"

"We both did," she said, but I knew I had little to do with it.

"It felt like a going-away present."

"Maybe it was."

"Did it feel strange watching me have sex with another woman? We haven't even made love yet."

"I thought it was hot," she moaned into my chest, her lip pulling softly against my skin, "watching you like that."

It would not be hot watching her with another dude, but maybe we could convince Eleanor to go down on her sometime while I watched. "Maybe tonight, you and I...?"

"I would like that," she answered. I rolled on top of her and we kissed, our bodies entwining, moving constantly, impossible to be closer without being inside each other. The way she grabbed my ass made clear how much she enjoyed my decision to ditch the shorts that night.

Lifting her gown above her waist, I feasted upon strawberry pie. A few weeks ago, we would have both come right away, but now we were able to prolong our enjoyment. My tongue, my face buried inside her moist, warm flesh. Her pearly button was so tiny I wondered if that was real or just in my mind, but decided I needed to find the answer to that question.

And her flavor! She had a taste all her own, sweeter than honey and hot as pepper sauce. That had to be all in my head, right?

Even at thirty, her legs were doe-like and so smooth, and my hands caressed them, spread wide as they were for me. I knew she would vanish the moment she came and, with her, my chance to make love to her, but I gave her the best tongue-lashing I knew how, because all I wanted was for her to have a bigger climax than anything any other man can give her.

Her body quivered, then shook from an internal earthquake, and I waited to wake up alone and drenched in my cum, tongue still digging deep, then returning to her clit. That's the strangest part, because she climaxed, screaming and writing around like the bed was on fire, but she kept begging me for more.

And I gave her more. And more.

A fist full of fingers pulled my head back, and her tongue licked my face clean of her juices. That was so f-ing hot. She needed me, I knew that now, just as I needed her. I wondered if this is what a heroin junkie feels, a desire this powerful that it consumes all else?

My sister was on top of me--don't ask me how, she just was, straddling my stomach warm and wet, my cock up against her chiseled ass. Her breasts swayed just a little, but were too firm to move all that much without more from her, but with her hands braced on my chest and staring into my eyes, I knew she was making a choice.

"I brought condoms," I said.

"Stop reading my mind," she answered, shocked but then she laughed, head back, boobs moving now. Then, totally serious, she warned me, "Don't make me pregnant."

She wasn't really there, was she? She was asleep in her own bed a thousand miles away, so she could not get pregnant. Not tonight. Right?

I remembered the lipstick, and there was no way for that to be around the root of my cock, either. Just as I decided to put on a rubber, she lifted up, reached around behind her to raise my love missile into firing position and impaled her perfect body on it.

Again expecting her to vanish in the first wave of pleasure, instead she started riding up and down. Slowly and in a perfect rhythm.

Warm goo splattered onto my chest, waking me in waves of pleasure too profound for words. My arms reached up to where she had been an instant before ten or fifteen jets of DNA intended for my sister instead sprayed lower and lower on me until the last few just leaked out into a puddle on my stomach at the tip of my satisfied cock.