Mile HighbyLost Boy©
My fingers dug into the arm of the chair as the engines of the aircraft roared and I felt myself being pushed down into the seat. The roar of the engines got louder and louder as we left the ground with a deep vibration that passed through me. I managed to open my eyes and get my breathing under control and relaxed my grip on the arms of my seat.
"First time?" came a gentle voice.
I looked up into the face of a gorgeous stewardess. I swallowed hard and nodded; she smiled and offered to get me a drink from the bar. I watched her walk away and smiled.
"Nice ass!" said a voice next to me. I looked over to see a stunning redhead who was smiling from ear to ear.
"What?" I stammered too stunned to say anything else.
"I said she has a nice ass." She repeated.
"Yes, yes she has a very fine ass." I agreed.
"Why thank you!" said the stewardess. I looked straight ahead into her eyes. She handed me my drink and leaned forward whispering in my ear.
"You should see my tits and pussy."
I took a healthy gulp from my drink before replying.
"I would love to." I somehow managed.
"Good!" the stewardess said, "Enjoy your flight."
I could still feel the heat from my blushing hot on my face as she turned and went about her duties.
"Lucky man," the redhead said.
"Yes I am." I told her.
"It appears you are ready for her right now." I heard her say.
I looked down at my crotch and there for any to see was my erection pressing against my blue jeans.
"Mmm my mouth is watering just thinking about your cock in my mouth." She moaned.
"Oh my god!" I whispered as my erection became harder still.
"Lover I would give anything to ride that cock of yours until we both came together!" The redhead moaned in my ear. I could feel the heat of her breath against my skin. I was practically shaking with need.
"And I would love to fuck you til you couldn't walk straight!" I whispered.
"God baby I am so wet!" she moaned again in my ear. Her breath was making my erection painfully clear now.
"Well look at you!" the stewardess said as she passed. "Do you want another drink?"
"Yes please." I moaned.
"She wants you," Said the redhead, "I need you!"
I bit my lip and tried to clear my head but when I closed my eyes all I could see was the stewardess riding my cock facing away from me as the redhead straddled my face letting me lick her soaked pussy. I could almost feel a hand stroking me lightly tracing the length of my shaft and suddenly I realized that someone was doing just that. I opened my eyes and saw the lustful glitter in the redhead's eyes as her hand rested lightly in my lap.
"It'll be dark soon and that's when the fun can really begin." The redhead said.
"My name is James by the way." I told her.
"I am Deirdre a pleasure," she emphasized with a gentle squeeze of my cock. "We are flying east so it won't be long until we catch up with the night."
"Yes," I moaned as she continued to pleasure me, "and when it gets dark..."
"I will unzip you, free that monster cock of yours and suck you off until you cum in my mouth. Oh and I will swallow every drop!" she said challenging me.
"What if you don't?" I asked her.
"What do you mean what if I don't?" Deirdre asked.
"I mean it sounds like a challenge the way you said that." I told her.
"Ah," she said thinking on the fly, "well if I can't swallow every drop you can... you can..."
"You let me fuck you in the ass." I inserted.
"Done!" She said fiercely. "And if I do?"
"I will spend two days of my vacation with you making you cum over and over again."
I could see her visibly shudder in pleasure. We shook hands just as the stewardess came over to check up on us. I finally caught a good look at her nametag and in friendly white letters it said 'Brenda'.
"So what is going on over here?" Brenda asked.
"We have a wager." I announced.
"What sort of wager?" she asked eyes wide with curiosity.
I motioned for her come closer so I could whisper it in her ear. When I did her eyes fixed on Deirdre, then me, and then back on Deirdre.
"Well what about me?" Brenda pouted.
The wheels turned and I smiled brilliantly and whispered once more into her ear. Brenda stood up straight and you could see she was pondering my offer.
"Okay but we have to be discreet." Brenda said licking her lips. She walked away and Deirdre gave me a quizzical look.
"What did you say to her?" She asked.
"I told her I wanted to join the Mile High Club with her." I said proudly.
"Before or after our contest?" Deirdre asked.
"After." I told her. "I have a lot of pent up hunger to let you have."
"Really? You are attractive and smart and hung like a bull how could you possibly be 'pent up?'"
"I have a very stressful job that doesn't allow for much down time." I told her.
"Oh, so this is a very important vacation for you." Deirdre said genuine compassion in her voice.
We both fell silent as the aircraft sped towards nightfall and my hunger grew and grew. Before I knew it the sun began to set and I can tell you there is no more beautiful sight. I leaned towards Deirdre to get a better look out her window. We shared that long moment as the sky was set on fire by the retreating sun and before long the reds and gold were replaced with violet and indigo and finally with utter blackness. I sat back in my seat, closed my eyes and replayed the sunset in my mind over and over.
I felt her hand on me suddenly. Her fingers moved slowly and without any hint of being hurried at all. I bit back a moan as my body reacted to her deft touch. The lights in the aircraft dimmed significantly and I leaned back and let her do all the work. Her fingers traced me at first getting me nice and hard before freeing me. She used a blanket to hide what she was doing the clever little minx. I let out a low sigh as I felt her fingers wrap around the shaft of my cock. She began to stroke me getting me even more excited than before. I felt the blanket shift a little and then there was her hot breath on me and her mouth swallowing the sensitive head of my dick. Her tongue swirled around the head as her hand moved up and down the length occasionally giving the shaft a squeeze. I fought to control my breath as I was really enjoying myself but didn't want to alert anyone else to what was going on. I opened my eyes just for a moment and there was Brenda watching us a wicked gleam in her eye. Then she disappeared from view and I closed my eyes once more. Deirdre worked about three inches of me into her mouth and her head did a little bob as she sucked me off. Her hand moved slowly up and down the shaft as her tongue teased me to new heights of pleasure.
"God it has been so long!" I whispered so only she could hear it.
She needn't respond as her lips and tongue said volumes. I reached under the blanket and ran my fingers through her hair and she moaned at this sending pleasure through my body. I continued to stroke her hair as she stroked my cock. If this was how she sucked dick I couldn't wait to feel her pussy wrapped around me for two days. I was lost in the pleasure once again and I could feel my orgasm getting closer and closer. It was like a rogue wave that threatened to hit at any time but I held it off by sheer force of will. Deirdre must have sensed how close I was or maybe it was my cock growing even thicker in her mouth. Either way she adjusted herself so that she could take more of the length down her throat and she began to deep throat me. I could feel her head bobbing up and down while her cheeks caved in while applying even more suction. My entire body began to shake and without a word of warning my dick sent jet after jet of hot cum down her throat. I could hear her swallow over and over again drinking up my semen like it was liquid gold. After my climax had subsided I lifted up the blanket to see her smiling face and one large drop of cum fall from her lips onto my jeans. I looked down and she followed my gaze and shrugged. I mouthed the words, 'your ass is mine' and she just smiled ear to ear. Deirdre tucked me in, zipped me up and positioned herself next to me.
"You really want to fuck me in the ass?" she asked finally.
"Yes I do." I told her.
"Well you are in for a treat then. Not only do I do anal but I enjoy it almost as much as vaginal."
"Mmm lucky me." I purred in her ear. "I meet a redhead who likes to do all the naughty things I have wanted to do for so damn long."
"I take it you have a thing for redheads too." Deirdre said smiling wickedly.
"Oh yes I do!" I said a bit too loud.
"Well check this out." She said pulling up her skirt revealing her soaked pussy with a racing stripe of red hair that matched that on top of her head. She dropped her skirt back down and snuggled back down next to me. We both drifted off to sleep after my powerful orgasm drained me of the stress I had clung to from three years without a vacation.
I woke up to a gentle touch on my shoulder. I looked up and saw Brenda smiling down at me.
"It's time!" she said in a conspiracy like tone of voice. I turned and saw that Deirdre had taken the blanket and was leaning up against the window. I rose to my feet and followed Brenda to the front of the plane. She pulled me into a bathroom and closed it behind us.
"We can't be very loud and there isn't a whole lot of room." She explained. Both statements were obvious and even as I looked around she was peeling off her underwear and bending herself over the sink offering me her pussy right then and there. My jeans hit the floor a few seconds later and I eased my cock between her pussy lips just a bit later. We both moaned as I penetrated her and she enveloped me. Her pussy was so damn tight and slick with need. There wasn't a lot of room for moving but I would make use of what we did have. Soon we had a nice rhythm going as I fucked that tight hole of hers in quick hard jabs of my hips. I could hear her grunt each time I was buried deep in her and that made me all the more hungry to fuck her silly. I looked down and watched as my cock disappeared into her and she looked over her shoulder and moaned softly, 'do you like the view?' I nodded as I flexed my dick inside of her and she had to cup her hand over her mouth to keep from screaming. I pulled out and spun her around and sat her atop the sink before drilling her pussy once more. I leaned close to her as my hips slammed as hard as I could muster. I moaned in her ear, 'like this cock of mine?' She nodded her reply as she clenched her pussy muscles to match my flexing cock. I felt my second climax begin to build and build. I told Brenda I was close and she told me the same. We wanted to cum at the same moment so we adjust how fast and hard I was thrusting until with a deep soul wrenching kiss we both came together. The kiss deepened as it kept us from screaming and alerting everyone on the plane as to our rendezvous. I kept my cock in her until both of our breathing and heartbeats got somewhere near normal. The kissed deepened and I felt myself harden inside of her much to my delight and her surprise.
"Again?" She moaned breaking the kiss.
"Unless you don't want to?" I said.
"No it's not that." Brenda said.
"Then?" I asked looking deep into her eyes.
"I have never met a guy who could go twice in a row after so strong an orgasm." She explained.
"Should I leave?" I asked her hoping she would say no.
"No... I just need to... I mean I want to..."
"Just say it." I told her.
"I want to swallow your cum just like that redhead did."
"Ah." I said softly. "Well if I let you do that then you have to accept the same challenge she did."
"What was the challenge?" she asked with a brilliant smile.
"If you suck seed, I mean succeed you get me for two days to be pleasured like no other."
"And if I fail?" she cocked her head to the side smiling all the more.
"I get to tap that fine ass of yours." I said.
"You mean anal sex?" She asked mockingly shocked.
"You got it one. You must swallow every drop though." I said.
"And what if I forfeit?" She asked leaning forward and chewing on my ear. "Will you fuck my ass anyways?"
"Yes I believe that would be the case."
"Hmmm. Well that being the case sit down and watch." Brenda said. I sat on the toilet and she turned to face away from me and used our mixed fluids began to lube up her tiny little asshole. She moaned softly as her index finger made little circles at first then applying more cum to her finger eased it into her tight hole. I watched her finger her ass and my cock got harder as my excitement grew and grew. I reached up and pulled her onto me letting her pussy juices lubricate the head and shaft of my cock. She rode me moaning as soft as she could.
"So big! I hope it fits into my tight little ass." She said.
"Let's find out," I said lifting her off my cock and adjusting the angle as she pulled her ass cheeks apart. I let her do all the work. I felt the head touch her asshole and then as she let more of her weight settle down it began to open and allow me inside. As she bent her knees the head 'popped' inside and Brenda gave a sigh of relief. Now it wasn't long at all until the entire length was buried to the hilt inside her tight little ass as she had called it.
"God I miss this feeling." She said to me.
"What do you mean?" I asked.
"I haven't let anyone do this in years. It's a trust issue."
"I guess you trust me."
"Yeah, you are a nice guy and I really wanted to feel a nice thick cock in my ass again."
My hands settled onto her hips as I began to lift and drop her on my dick. Once again she bit back a scream of delight as I fucked her ass. But it wasn't long before she was fucking my cock with her ass. She was riding me without any hesitation driving me deeper and deeper with each downward slam of her hips. I had to grit my teeth and fight the urge to cum as she dropped down faster and harder.
"Like that lover?" she moaned over her shoulder.
"Oh god yesss..." was all I could get out.
"I want you to fill my ass with your cum! I can't wait come on fill me up just like your cock is filling up my ass!" she growled to me.
I began to pant and break out in a cold sweat. This orgasm was going to be a lot stronger than the other two. I felt her ass get tighter as my cock started to swell. With a little moan of surprise she knew I was close. She was grunting steadily now and when I grabbed her and started to fuck her ass but thrusting upwards she met me halfway and then with one hard final thrust I rammed my cock as deep as it could go and came deep in her ass. I felt her stiffen when I came and she was right there behind me. How we kept from screaming is still a mystery. I was panting in her ear muttering how great it had been how tight her ass was and worshipped the ground she walked on. She responded in kind and slowly eased off of me and we both cleaned up checking the other to make sure we were passable to exit the bathroom. She snuck another soul deep kiss on me before opening the door and exiting when no one was watching. I waited before leaving so it wasn't obvious to what had happened. I reached my seat and slowly sat down so as not to wake Deirdre but she opened an eye and smiled.
"So? How was it?" She asked waiting for all the gory details.
"If I say something won't you get a little jealous?" I asked.
"No, it will only make me more determined to rock your world." Deirdre said smiling.
"Well if that is the case, it was amazing! She couldn't go down on me but man was her pussy tight and..." I stopped before I mentioned fucking her in the ass.
"...and? And what?" Her deep green eyes looked into mine.
"She has a very tight little ass." I said.
"Oh does she now?" She said. "Why did she let you fuck her ass if she didn't suck you off?"
"I told her about the challenge and she forfeited." I said.
"Oh that little... She's a smart one. I hate to lose but the thought of your thick cock deep in my ass has got me all wet again."
"Good, but right now I need to rest before I tap that fine ass of yours."
"Rest. You are going to need it. I am going to eat you alive."
"Yeah me." I closed my eyes and drifted off to a wonderful sleep for the next five hours as the plane raced across the night towards Ireland and my family home.