Her Mile-High Club Initiation

I had never seen her prior to that day. Ever since she sat her beautiful ass next to me in the cockpit, I knew we'd be in for some turbulence. Being the captain has its benefits, for sure.

The airline had merged with another company recently, so more and more new faces were appearing as my co-pilots on various flights.

"Welcome aboard," I said. There was no way I was going to hide the fact I was hard in these airline-issued slacks. They were too snug.

Captain Valerie Destin smirked and didn't even respond. She stood around 5'5" and was thick in all of the right places. She had nice-sized breasts she tried her best to hide in her company-issued blazer and a beautiful round ass that was suffocated by her dark blue pants. She smelled heavenly and was naturally enchanting. No makeup and a ponytail.

"I'll handle takeoff," she stated. I was used to my first officers flying as I observed and double-checked their work. She had an energy that demanded respect. It truly turned me on.

Valerie placed her headset on and proceeded to radio the tower.

Takeoff was amazingly smooth. I was actually jealous at how seamlessly she maneuvered the aircraft. I had been flying for fifteen years and had not accomplished the effortless command she had. Even more of a turn-on.

"You're not much for words," I said, glancing at her to the right and then quickly returning my attention to the front of the aircraft. I was not trying to get any HR complaints. I needed to keep this professional, no matter how hard my dick was. It was pretty annoying, honestly.

Think of something else, Harold. You're being obvious.

"I'm just focused, Captain Russell," she responded. Valerie initiated autopilot and removed her hands from the console. She rested and reclined in her seat and breathed a sigh of relief.

"Now that we're on autopilot and we're at 30,000 feet, I can fucking relax," she said. "It's stressful being a female pilot. I have to demand respect, while men like you just show up and receive it."

Her voice exuded a blend of confidence, sexiness, and curiosity that intrigued me. Her eyes revealed both power and submission. The perfect balance.

I relaxed in my seat as well and this time, returned her stare.

"Touché," I responded. I guess I could be brief as well. "Flawless takeoff, by the way, Captain Destin."

"I appreciate you referring to me as Captain, even though I am the first officer on this flight," she said, smiling. "Brownie points."

"I know if you fly like that, you're obviously used to commandeering the aircraft," I replied. "I assume you're using this flight as a connection?"

"Correct, Sir," she said.

She removed her headset and turned around to confirm that the cockpit door was shut.

"Between you and I, it's my last flight for the airline," she whispered. "I've been given another opportunity overseas that is more lucrative and worth my time."

"Congrats, babe," I responded.

Fuck.

"I was waiting for you to loosen up," she chuckled. "That bulge in your pants showed your interest in me ever since I walked my ass in here. Don't worry. All that goes on in the cockpit stays in the cock... pit. Pun intended."

The bulge in my pants now revealed a precum stain.

"Take off your headset, Russell," she said, as she began to unbutton her blazer.

"Yes, Ma'am," I nodded.

She removed her blazer and placed it on the floor. She unfastened the top five buttons of her shirt to reveal her plump, juicy breasts. The shirt was truly suffocating them. I was glad she was letting those beautiful girls breathe.

She pulled out her left tit with her right hand and placed her left hand on my cock, which was still protruding from within my pants.

"I can feel your precum," she sighed. "That shit turns me on. I want to taste it."

I stood up beside her as she fumbled with my belt and pulled down my pants. I had never done anything like this in the cockpit. I'd definitely had sex with flight attendants in hotels, but nothing like this in flight. Thankfully, there was no turbulence.

She pulled out her other tit and let both hang over her half-buttoned shirt.

"I've had a crush on you from afar, Harold," she said, looking up at me. "Rub my nipples while I suck your dick."

I pinched both nipples softly and then squeezed harder as she took my tip into her mouth. A bit of precum dripped onto her lap as she gripped my hard cock. Jerking back and forth roughly, she slowly licked the tip of my cock in a seductive circle before gulping my entire shaft in a quick deepthroat.

"Oh, fuck, Valerie," I moaned, louder than I had wanted to. She felt fucking amazing.

Squeezing my manhood, she pulled me out of her mouth and looked up at me, smiling.

"Your cum is sweet," she said, licking her lips. "Unfortunately, I'm on my period."

What?

"I think this cum belongs in my ass," she said, as she began undoing her trousers. "Would you agree with that, Captain?"

"Fuck yeah, I agree," I said. It was time to turn things around and take charge of this liaison.

Grabbing her ponytail, I bent her over her seat, causing her huge breasts to lay across the controls in front of her. Grabbing the back of her pants and panties with my free hand, I yanked them down to reveal her beautiful ass. She had a tattoo on her right cheek. She was fucking exquisite.

"Lube up your cock with your saliva and go in slow," she demanded. She gripped both ass cheeks and spread them, revealing a perfectly shaved ass crack. Not too tight, not too wide.

"Spit on my hand," I said, placing my palm beneath her lips.

She opened her mouth and spit out saliva into my hand. Once enough had gathered, I placed it on my cock and rubbed it up and down. This should do.

"Spread that ass more," I said.

"Yes, Sir," she moaned.

I pushed my throbbing tip into her tight asshole slowly. It fit like a glove.

"Yeah, that's fucking perfect," she sighed. "Like that, baby."

"Like that?" I asked.

"Like that," she replied. "Now shove it in. No mercy. We don't have much time."

I pushed my cock in hard and deep. It was the first time anal sex truly felt like a pussy. That lube had been perfect, as I slid into her ass seamlessly.

I pulled and pushed hard and fast as I watched her ass cheeks widen with each thrust. She had an amazing ass and sexy body. I only hoped I could last a respectable time, because everything in me wanted to cum.

"Ahhhhh," she moaned.

"Fuckkk," she gasped.

She was too loud. I covered her mouth with my left hand and pulled her hair back with my right as I proceeded to ram in and out of her.

"Yeesssssshhhhhh," she moaned in a muffled voice, as I tried to cover the ascending volume from her mouth.

"Ohhhhhh fuck!" I yelled. What a hypocrite I was, covering her mouth when I was being just as loud.

The scene playing out was raw debauchery at its finest. Valerie's tits swung back and forth in front of her as my cock rammed into her dripping, wet ass crack as she bent over the seat. One hand pulling back her ponytail and the other in her mouth. She was sucking my fingers while she moaned.

I was feeling the sensation of boiling cum tingling at the tip of my cock, ready to explode.

"You sure you want this cum in your ass, Captain?" I sighed, out of breath and struggling to hold in the impending explosion.

"Mmmhmm," she stared back at me. Her seductive, inviting look was all I needed to release my babies inside of her ass.

Landing was smooth. I never saw her again, but did hear of her ascension through the ranks in the coming years at her new company.

She's now the Vice President of a rival airline. I'm proud of her and thankful for our mile-high memory.