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Pre-flight and In-flight drinks lead to joining the Mile High Club
“Welcome to Boston. The current time is approx. 7:00am, and the temperature is a cool 45 degrees. We will be taxiing a few more minutes, so please stay seated until the Captain has turned off the fasten seat belt sign. Have a nice day in Boston.” came over the airplane speakers.

As I was waiting for my bag to arrive, Ylena secretly blew me a kiss from across the carousel, mouthing thank you as her boyfriend was pulling her bag off the line.

I winked at her and couldn’t help reminiscing about what happened on my “Redeye” flight….

I arrived at PDX for my late-night flight to Boston the customary “two” hours before the flight departed. The airport was empty at 8:00pm on a Tuesday night in July. After passing through security, I headed for my gate. I arrived at the gate with enough time for a couple cold brews.

It’s a crime to charge $8.00 for a pint of beer. I was halfway finished with my beer, alternating between watching planes take off and people watching when I heard, “I will have a Cape Cod please.” I turned my head to follow the voice and took a double take. There was a gorgeous brunette sitting a couple seats down from me. She caught my gaze, looked at me and smiled. I turned my attention back to the runway where a 747 was landing. I finished my pint and asked the “beer” tender for another. This time I turned to catch her starring at me. I finally spoke, “Hi!”

She responded in kind. I took a couple of drinks before speaking again. “Are you on the red-eye to Boston?”

After I said that, I thought to myself. ‘Idiot’, of course she’s on the red-eye why else would she be sitting here.

“Yes,” she replied. “I hate these overnight flights. They screw up my sleep pattern,” she continued.

I took another swig, and said “Yeah, I here ya. It’s so damned hard to sleep on planes.”

She finished her drink and ordered another. After a beer and ½ duty called and I went to use the restroom. I was feeling a little buzzed from the alcohol and thought if maybe this will be the flight where I join the exclusive “Mile High Club”. I often fantasized about sex on an airplane. Part of the excitement is the thrill associated with the possibility of getting caught. I finished relieving my bladder and headed back to the bar. I still had 45 minutes until boarding.

After hoisting myself back on the bar stool, my bar mate asked me where the restrooms were. I responded and used my index finger to point the way.

I finished my pint. The “beer” tender asked if I wanted another. I looked at my watch again and determined I had time for one more.

My bar-mate returned. Her face looked a little flushed. Apparently, the vodka was taking affect. She finished her second drink and turned to ask me if she had time for another. I glanced at my watch again and said, “We have about 30 minutes before boarding. I think you have enough time.”

She said, “Great!!” She then asked the bartender for one more.

“I’m Brian,” putting my hand out for a shake.

She moved her hand towards mine and said, “I’m Ylena.”

“Elena?” I ask, not sure of whether that was right or wrong.

“Ylena with ‘Y’,” she repeated.

“That’s a beautiful name,” I state.

She responded, “I will let my mother know. She really loves my name.”

“Flight 1512 to Boston will begin boarding in 15 minutes,” came over the airport speaker system.

I had about ½ of beer left and Ylena had only taken a couple of sips from her freshly poured drink.

“I already have quite a buzz going from the previous two drinks,” Ylena offered. “It looks like I’m going to have to slam this one,” she continued.

I chuckled a bit and responded jokingly, “Don’t worry. I will carry you to the plane if you can’t walk.”

“Don’t gets your hopes up, I think I can walk just fine,” she said with a chuckle of her own.

I finished my beer, paid my outrageous tab, letting the “beer” tender know my feelings about the highway robbery of $8.00 per beer. “I better use the bathroom one more time before boarding,” I say to Ylena. “It will be a while before they let us get up and use the bathroom.”

“Good idea! I better do the same,” Ylena commented. “I’ll see you on the plane.”

Letting my lizard drain, I started imagining (hoping) this would be the time my “mile high club” fantasy comes true. When I take “Redeye” flights, I always try to get a seat at the back of the plane. One reason is hoping someday I will get to live my fantasy, and the other if the flights not full, I usually get a whole row to myself.

“Flight 1512 with non-stop service to Boston is now ready for boarding. Please have your boarding pass out and available to the gate attendant,” came over the boarding area. I got in line, and was desperately looking for Ylena. I didn’t see her as the line got smaller and it was almost my turn to board. My mind was convincing me she had way too much to drink and was puking or passed out in the restroom. Finally, it was my time to board and still no Ylena. I immediately thought another trip without joining the “Mile High Club”.

I found my seat and my suspicions were right. No one else was in the row; I had it all to myself. “Damn!! Where’s Ylena?”

The last few passengers were coming aboard, and the flight attendant announced that everyone was on board and the door was being closed.

‘SHIT’ I thought. She must have gotten really sick. “Everyone must be seated before we can leave the gate area,” was announced. I fastened my seat belt and was reading the in-flight magazine when I heard, “I bet you thought I was sick.”

I turned to my left and Ylena was walking by my row. She stopped a few rows up, looked back at me and smiled. I was relieved she was okay. I was also euphoric that my fantasy still might come to fruition.

Take off was normal, and after we reached cruising altitude, the captain announced he was turning off the seat belt sign and we were free to move about the cabin. I immediately unbuckled mine and headed toward Ylena. When I reached her, she must have known I was going to come up. She had a big smile on her face, and she was chuckling.

“When did you board the plane,” I boldly asked.

“I have an MVP card and boarded with First Class,” she retorted.

‘I looked for you when I was in line. When I didn’t see you, I thought you must have gotten sick,” I told her in a concerned tone. “When I didn’t see you board, I thought you passed out.”

“Thank you for being concerned about me,” she responded in a smartass tone. “I’m a big girl and can handle my alcohol just fine.”

“Great,” I said. “Why don’t you come back to my row? No one else is sitting in it and I will buy you another drink.”

She looked at me inquisitively, deciding whether she should or shouldn’t.

“Come on, it’s a long flight,” I say. “Let’s test whether or not you can handle your alcohol.”

She unbuckled her seat belt, got out of her seat and followed me back to my row. I sat in the aisle and she by the window. We chit-chatted a few minutes before the flight attendants made it back to our row with the drink cart.

“May I get you two something to drink?” Stephanie, one of our flight attendants, asked.

“I’ll have Cranberry/Vodka,” Ylena said. That is a Cape Cod, but Ylena figured Stephanie wasn’t a bartender, so she made it easy on her.

“I’ll have red wine,” I said.

Ylena immediately changed her mind. “On second thought, I will have red wine also”, she told Stephanie.

Stephanie handed us our wine and said, “That’s $10.00.” I my Visa card and included an extra $2.00 for her. Of course, she responded that it wasn’t necessary to tip. I told her I understood, but we will want more later.” She said, “No problem. The plane is half full, so just hit the call button when you want another.”

We poured the wine into the plastic cups and clanked them together saying “Cheers.”

We chit-chatted a few more minutes while we sipped our wines. After the glasses were half empty, I knew it was now or never if I wanted to make this fantasy come true.

In my beer and wine induced state of mind, I said to Ylena “Are you a member of the ‘Mile High Club’?”

“What airline has that frequent flyer program,” she asked.

I was dumbfounded. Ylena doesn’t know what the mile high club is, I thought to myself. Interesting!!

“The Mile High Club is not associated with any particular airline,” I say. “You don’t get miles or trips or prizes, and it doesn’t cost anything to join,” I continue coyly.

“Well, what’s special about joining this club,” Ylena asks as she sips another drink of wine.

“Do you two need another glass of wine,” I hear from behind me.

I turned my head, and said, “Yes Stephanie, that would be great.”

Stephanie left, and Ylena repeated her question.

“The Mile High Club”, I start to say when Stephanie returned with our wines. I handed her my Visa card, when she said, “These are on the house. I’ll be back to check on you in a little bit.”

We both said thanks, and I commented. “See, it does pay to tip.”

“Ok. Now what about this Mile High Club?”, Ylena questioned again.

I motioned her to lean closer to me. I explained what the club was and what it takes to join. Ylena stayed motionless for a few seconds, and then moved away from me. It was quiet for a few seconds after that.

“I’m sorry, I didn’t mean to offend you,” I stated. She looked at me; a big smile came over her face. She motioned me to move closer. Much to my surprise, she planted a big, erotic kiss on my lips. Instantly my cock felt the jolt of excitement.

“That sounds very, very naughty,” she said in a low sultry voice. “I’m getting wet thinking about it.”

“I’m not getting wet, but it is having that ‘male’ affect on me,” I retort.

With that she glanced down at my crotch and could see the “tent’ already formed. When I travel at night, I purposely wear button down jeans with no underwear, making easier access if needed. With her eyes fixated on the tent I was forming, she reached out and grabbed a hold of my throbbing member.

“WOW!! You’re ready for some action,” she said.

Fair is fair, so I reciprocated and moved my hand to her crotch. Once she saw me moving my hand, she spread her legs. The second my fingers touched it, she let out an audible moan. She was already wet.

“I can return the WOW!!” I said. “Are you wearing any panties?” I continued.

“I never wear panties,” she replied. “Where do we go from here,” she whispered to me.

“Move your tray down from its seat,” I commanded. “Here’s my glass, set them both on the tray.”

The plane was almost all dark, except for a few night owls reading. I stood up and opened the overhead bin to grab a couple pillows and a blanket, and put the arm rests up.

I put my arm out, as if to hug her, and asked to slide closer to me. She now sat against my shoulder, and I put my arm around her.

“Pull your pants down”, I instructed her. She complied with my instructions and I put the blanket over her body. I put my hand under the blanket and found her wetness. She started to moan. She spread her legs and turned her head towards me. I unbuttoned my pants, just enough so she could grab my hard cock.

“That feels awesome Ylena,” I whisper to her.

I continued my play of her very wet pussy. I ran my middle finger up and down her wet slit very slowly. She was moaning louder and her breathing was becoming shallower.

“Do you know what you’re doing to me,” she asks incoherently.

“YES!!” I respond. “Enjoy it!!.”

After a few minutes of teasing her, I found her clit and trapped it between my index finger and middle finger. I began making circular motions. She was obviously in another world now. She started bucking, moving her ass on and off the seat. She was close to cumming.

She kept repeating, “OH MY GOD!! OH MY GOD!!”

She opened her eyes, turned her head looked up at me and said, “I’M GOING TO FUCKING CUM RIGHT NOW!!!!!!!!!!!!!!!!!!!!!!!!!!!!!”

Boy did she ever!! Her whole body was shaking. We ran into a little turbulence and she was making her own. My hand was soaked. I slowly stopped my assault on her wet lips and held my hand and against her mound until she stopped convulsing. She released my cock for a moment, enough to catch her breath and thank me over and over again. I took this opportunity to taste her nectar. I brought my fingers to my nose and inhaled it like sniffing the bouquet of a fine wine. It was an intense aroma. I think the passengers a few rows up could smell it. I put my fingers in my mouth and licked them clean.

“God you taste incredible,” I lustfully said to her. “I can’t get enough.”

She tossed the blanket to the side and her beautiful wet pussy was exposed to the re-circulated air. I reached down and slipped my finger into her wet hole. I brought those to my mouth and enjoyed the taste again.

She grabbed my cock, and with lust in her eyes she said, “YOU NEED TO FUCK ME RIGHT NOW!!!”

Just then I heard a voice to my left. “Yes, you need to FUCK her!!”

It startled us both. Ylena sat up and reached for the blanket to cover herself. I turned my head and saw Stephanie, our gracious flight attendant, sitting across the aisle. Her legs were spread, and she was slowly rubbing her nylon covered snatch.

I turned a few shades of red. And I didn’t have to look to know Ylena was just as embarrassed.

Stephanie repeated, “She definitely needs to have your hard cock inside her!!” She continued, “Come with me I can help.”

We were both obviously still aroused. I tucked my tool back in my jeans. We both got up and followed her around the corner to the back galley. Once there, she pulled a curtain across so nobody could see in. Then she got on the phone to the other flight attendant up front and told her the toilet was plugged up and to make an announcement that the back bathroom was going to be shut down for the remaining hour of the flight. The other flight attendant did as instructed.

By now, my cock had become semi-hard. Stephanie looked at me and said, “You can’t fuck her like that.”

And in one motion, she dropped to her knees, pulled my pants down, and took my cock in her mouth. A few long, wet strokes and I was ready again. She pulled off my cock, and it hit my belly. She then went over to the jump seats where the flight attendants sit during take offs and landings. She pulled it down and instructed me to sit down. She then turned to Ylena and said, “He’s all yours honey!!”

Ylena looked at my hard cock, smiled and removed the blanket covering her, and pulled her shirt up past her tits. There was a little more light in the back galley than the seats. Ylena’s body was better than I thought. Her tits were firm and her nipples hard as pencil erasers. Her pussy hair was still glistening with the wetness from her intense orgasm. Stephanie couldn’t help but notice also.

“You’re gorgeous!!” she said.

Ylena came over to where I was sitting and stuck her tits in my face. I reached up with my hands and grabbed them. I started squeezing them and alternating sucking each nipple. Her breathing was intensifying. She slowly turned around and stuck her sweet ass in my face. I squeezed and kissed each cheek. She then moved it slowly down my chest, past my stomach and proceeded to mount me. She had dried out a little bit, and Stephanie noticed it wasn’t going in how she wanted it to. She moved to Ylena and said, “Let me help honey.”

Stephanie then she stuck her middle and index finger in her mouth to wet them. Seductively making a fucking motion, after they appeared to be wet enough for her, she moved them to Ylena’s pussy and proceeded to insert them in her cunt. Ylena began moaning as Stephanie was penetrating her sex. It didn’t take long before you could hear the juices flowing. She pulled them out and told Ylena, “FUCK HIM NOW OR I WILL!!”

There was no way Ylena was going to give Stephanie the opportunity. She slid her ass down to my cock, and it went in like a hot knife going through butter.

“Your hard cock feels soooo good,” Ylena moaned as she slowly fucked me. .

“Yeah baby, nice and slow,” l moan back.

I heard a buzzing sound. I looked over to Stephanie and she decided to join the fun. She had removed her nylons, pulled up her skirt and was using a vibrator on her pussy.

Ylena noticed as well and started fucking me harder.

“I’m not going to be able to hold out much longer”, I state.

“YEAH, FUCK HIM HONEY!! FUCK HIM GOOD!!” Stephanie piped in.

I looked over at Stephanie and her eyes had that “glazed over” look like she wasn’t going to be able to hold on much longer either.

God her ass feels great as I help her move up and down my wet pole. “OH SHIT!! YEAH!! HERE I CUM!!!!!!!!!!!!!!” Ylena yells as her pussy squeezes my cock.

“ME TOO!” I say back as my cock shoots load after load into her wet, orgasming pussy. “AH!!!!!!!!!!!!!” I moan as my last load leaves my body.

Stephanie yells out, “MY TURRRNNNNNNNNN!!!

She was a squirter. Cum started streaming out of her pulsating cunt a good foot in front of her. It went on a few seconds as her body finally stopped spasming..

Ylena’s breathing continued to labor as she turns her head to me and speaks fragmented, “I’m -- still ---cumming. Can you -- feel me?”

She stopped fucking me and sat on my lap with my cock still inside her. “Yes, I can still feel you spasming,” I respond.

After what seemed like 10 minutes, she stopped orgasming. My cock had already begun its descent to normal size, and when she sat up, it flopped out and hit my leg. Man it was wet!!

Stephanie came over to me and put my semi-hard cock in her mouth again. She sucked it up and down a few times, taking the last few drops of the cum that remained in my cock. Not to mention lapping up Ylena’s juice. She then stood up and kissed Ylena on the lips, hugging her close at the same time. She told me to stand up and did the same to me.

“Thanks for the best flight I’ve had in a while,” Stephanie told us both.

“This is the captain. We will be beginning our decent into the Boston area in a few minutes. If you need to get up and use the restroom, now would be a good time,” came over the intercom.

“We have few minutes before he turns on the sign. Do you mind if I fuck him now,” she asks Ylena.

Ylena responded, “I think he will need some help getting ready.” My cock was in no condition to properly fuck Stephanie.

With that Ylena dropped to her knees and stuck my cock in her mouth. With the thought of becoming a Mile High Club member twice on one flight, and her expert cock sucking, I was hard in seconds.

“I think that will do,” Ylena stated.

Stephanie had been playing with herself while Ylena was getting me ready and was aroused and ready to take me. She turned her ass toward me, bent over and braced herself against the wall with her hands.

“FUCK ME BABY!! FUCK ME HARD!!” she commanded me.

I jammed it in her. She let out a load moan. Ylena was encouraging me, “THAT’S IT. FUCK HER HARD. SLAM THAT HARD COCK INTO HER. MAKE HER SCREAM…”

Stephanie repeated Ylena’s request, “YES!! YES!! FUCK ME HARD. KEEP GOING!! DON’T STOPPPP!!!

She was almost at the point of hyperventilating. “I’M CUMMMMIINNNGGGGG!!!!!!!!!!!!!!!!!!!” she yelled.

She was squirting again I could feel it against the shaft of my cock, as well as the droplets hitting the floor.

Her cunt was squeezing whatever cum I had left into her. My cock was getting soft fast, and Stephanie lifted off me. Apparently, I still had some cum dripping out, and Ylena didn’t miss a beat. She immediately licked it up, making sure not to miss a drop. She then put my softening cock in her mouth like Stephanie did and “cleaned” me off.

“Lady’s and gentlemen, as you can tell we’ve begun our decent into Boston. I’m turning on the fasten seat belt sign. Please return to your seats and make sure your seat belt is securely fastened. We will be landing shortly,” the captain said.

Ylena and I composed ourselves, and staggered back to our seats. We were spent. Stephanie dressed and started making preparations for landing. When the other flight attendant made her way down the aisle collecting cups and garbage, she noticed Stephanie wobbling a bit as she made her way past her to the front. I couldn’t hear what was being said, but it looked liked the other flight attendant was worried about her health. Stephanie waved her off and continued to do her job.

The plane landed safely at Logan International Airport. Stephanie was greeting passengers as they were deplaning. As I passed her, I said “Thanks for GREAT SERVICE!! I’ve never been on a Redeye flight wear a flight attendant was so attentive to my needs.”

Stephanie responded, “You’re very welcome. Come fly with me again.” I could tell her fellow attendant seemed puzzled.

Once in the gate area, Ylena hugged me and kissed me. She had to do it then because, apparently, she had a boyfriend, and he was meeting her in the baggage claim area. We exchanged business cards and headed separately to the baggage area….

“Excuse me sir, that’s my bag,” broke me out of my reminiscent trance.

“Sorry,” I respond as I step aside.

Finally, my bag arrived. I looked to see if Ylena was still in the baggage area. She was walking hand and hand with her boyfriend.

Hopefully she’s going back to Portland on my flight..
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