hooking up with [m]y [f]light attendant

In my previous job, I flew a lot for work. This had certain advantages, including often flying business class, racking up tons of miles, and this story, which I always remember fondly.

I was on an evening flight on my way out to my company’s headquarters city. I was eyeing the flight crew a bit and there was one stewardess who really caught my eye. She had her blonde hair tied back in a bun, had her hat askew just so, was wearing her skirt just a bit higher than her coworkers, and was rocking her heels.

As she worked the cabin I flirted a little bit when she came by, but nothing unprofessional. She was friendly, but she was also on the job, so I left it at that.

After the flight landed, I left and picked up a rental car and headed to the hotel near the airport. I checked in and headed to the hotel bar for a quick drink, and much to my surprise that stewardess was there! … but she didn’t look too happy.

I walked up to the bar. “This seat taken?” I asked, indicating the one next to her.

She looked up, and her sour expression brightened a bit. “Oh, no, be my guest.”

“Thanks,” I said, and ordered my drink. I paused for a bit and took a sip before asking, “Long day?”

She sighed. “Yes and no. The day was fine, but this hotel managed to stress me out. They lost my reservation somehow. I’m waiting for them to find me a room.”

I cocked my head to the side. “Really? Don’t the logistical superstars at the airline make these reservations for you?”

“HAH!” she blurted out sarcastically, loud enough to draw a few looks.

I chuckled. “I think I know what you mean. The people who handle business travel where I work couldn’t book the ham into a ham sandwich. One time they booked me a hotel in the wrong state.” She laughed a laugh that seemed genuine. I paused again long enough for both of us to take a drink. Then I held out my hand. “I’m NaughtinessAlt.”

She smiled and took my hand with her white gloved one. “I’m Jane,” she said.

We got to drinking and talking and it turned out that we had grown up in the same area, so we had some things in common. Our senses of humor seemed to just click and I loved her smile, so I tried to make her laugh as much as possible.

After about an hour and a half of drinking and talking I said, “so they seem to be taking a long time with that room of yours.”

“Yeah,” she replied, “they said that they’d call me once they had figured it out.”

“Hrm.” I considered my options for a second. Oh, what the hell, I’ll probably never see her again if she shoots me down so I may as well go for it. “Do you want to wait for that call up in my room? I hear the mini bar selection is to die for.”

Jane looked at me with a sidelong look. “Yeah, I’d like that,” she said after a few seconds that seemed like an hour.

“Great. Let’s get out of here,” I said, and we headed towards the elevators.

We got in and I pushed the button. The doors closed and as the elevator began to move I couldn’t hold my anticipation any more. I turned to her, moved my hand to to the small of her back, and pulled her in, kissing her deeply. She moaned her approval and pushed her tongue into my mouth, and I did the same. We breathlessly made out as the elevator glided to its destination while I felt her ass through her uniform skirt.

The elevator dinged and the doors opened, and it was all we could do to tear ourselves away from each other long enough to stumble out into the hall. We staggered towards my room, with our luggage, and I managed to get her up against the wall every few doors. I unbuttoned her jacket and grabbed her tits through her blouse as we continued to half make out / half stagger to my hotel room.

We finally made it to my room and I unlocked and opened the door. We entered and I closed the door behind us. Jane unbuckled my belt, unbuttoned my pants and pulled them and my underwear to the floor. She stroked my cock, which was rock hard by this point, slowly as we made out in the entryway of the hotel room. She was still wearing her gloves, which were soft and gave a unique sensation I’d never felt before. I groaned my approval as our tongues danced.

She placed a hand on my chest and gently pushed me back. “Wait,” she said, and rebuttoned her jacket and put a stray strand of hair back in place. I looked at her quizzically, before she dropped to her knees and took my cock in her mouth. She looked up at me as she slowly slid her lips down over my shaft.

She started to bob up and down the length of my cock, all the while looking up at me with her beautiful blue eyes, her hair still neatly tied back in a bun. “Oh fuck,” I groaned, and leaned back against the wall. She started to swirl her tongue around the head of my cock on her upstrokes, and fondle my balls with her free hand, and the only thing I could think about was that this was the best head I had ever received in my life.

“Fuck, you’d better be careful,” I warned. She briefly hummed her acknowledgement but she seemed to ignore my concerns, continuing to service me with just as much vigor. I put my hand on the back of her head and groaned deeply again. I wasn’t going to last much longer, so I pulled out of her mouth (taking about all of the self-control I had). I needed some time to recover, so I pulled her to her feet and hiked her skirt up around her waist, then pulled her panties to the floor and sat her on the bed. I got down on my knees and kissed the inside of her thighs, and she ran her hands through my hair as I slowly moved up until I got to the folds of her pussy.

When I got to my destination, I pushed my tongue inside her and she moaned deeply and fell back on the bed. She was already soaking wet, and I savored the taste of her juices. She began letting out moan after loud moan as I ate her, lapping at her clit. It wasn’t long before her moans started getting shorter and higher pitched. Finally, she squealed the cutest little squeal I’ve ever heard and came on my face, squeezing my head between her thighs.

Eventually she came down from her orgasm and released me. “Your tongue is amazing,” she said. I laughed a bit at that (though inside I was high-fiving myself). She reached down and grabbed my cock, and stroking it she said, “now I need you to fuck me. You want to be inside of me, don’t you?”

I definitely did, so I turned her around so she was on her hands and knees on the bed in front of me and lined up behind her. I hiked her skirt up again and slid my cock head over her slit, making her moan loudly. The moan became a whimper as I grabbed her hip with one hand and slid inside her. Her wet warmness felt incredible around me and I began to pick up the pace. I gathered her hair in my fist and pulled her head back as I railed her, causing her to cry out in a mixture of pleasure and pain. The sound of skin slapping skin soon filled the room as I pounded her. She was letting out a small yelp every time I thrust deeply into her. I was actually thinking about how uncharacteristically long I was lasting when I felt her pussy clench down on my shaft and she grabbed the sheets with her hands and screamed as she came helplessly on my cock, making me feel like a god.

She sort of fell off my cock and caught her breath before looking up at me. “You haven’t cum yet!” she said accusatorially.

I shrugged. “I’m making an unusually good first impression, trust me.”

She laughed. “Well, that just won’t do,” she said. She pushed me back on the bed and started to strip, taking off her uniform jacket and blouse, stepping out of her skirt, which was now damp with our juices, and taking off her bra, until she was standing in front of me in just her heels, gloves, and uniform hat. Her breasts, largely concealed until now, were perfectly perky without being overly large, and I just lay on the bed taking in her beauty for a few seconds.

“Christ you look good,” I said. She giggled and climbed up onto the bed to straddle me. She lined my rock hard cock up with the entrance to her pussy and then slowly sank down onto me with a sigh. She was just as perfectly wet and warm and tight around me as she was when I was taking her from behind, but now I could see all of her. With one hand I grabbed one of her breasts and gently rolled her nipple between my thumb and forefinger and with the other I held her above her hip as she began to ride me. Every rock of her hips gave me a wave of pleasure as her pussy slid up and down my shaft, and I moaned, making her grin in self-satisfaction.

“Did you like fucking me in my uniform?” she asked mid-ride. “It always makes me feel like such a little slut when I get fucked in it.”

“Hell yeah I liked it,” I grunted. “Are you my little slut stewardess for tonight?”

“Fuck yes I am. I aim to please.” She leaned down and kissed me deeply with my cock still inside of her. “And your little slut stewardess isn’t going to stop servicing you until you cum for her.” And with that she quickened her pace.

The dirty talk coupled with her perfect body and the exquisite feeling of her pussy riding up and down my cock were too much. I could feel my orgasm building, so I grabbed her hips and pulled them down onto me as I came, shooting my cum deep into her and groaning, as she cooed, “that’s right baby, cum for me.”

“Holy shit,” I said once I’d caught my breath. Jane took off her heels, hat, and gloves, and let her long blonde hair out of its bun.

Now totally naked, she laid down next to me and whispered in my ear, “so was I a good little slut for you?”

“God yes. It’s a good thing my first meeting isn’t at the crack of dawn. Christ, I hope you don’t have to fly out too early tomorrow.”

“Don’t worry, it’s not until the afternoon,” she said, and leaned in to kiss me softly. We shared a few kisses but were soon asleep.

I hadn’t closed the blinds, so in the morning when I woke up sunlight was streaming through the window. Jane was lying asleep with her back to me, the sunlight catching her hair. I scooted up to her and began to kiss the back of her neck, causing her to stir and mumble “mmmm, good morning”. I chuckled and let one hand drift down to between her legs, starting to gently brush along her slit and clit as I continued to hiss her neck. Slowly she grew wetter and her breathing more intense, until she spread her legs to admit me better access and I slid a finger inside her, causing her to moan. I found her spot and slowly stroked it, and she turned her head to kiss me back as I fingered her. She reached back and started to stroke my cock as well.

Eventually she pulled my hand away and rolled onto her back. With her hand on my cock she guided me between her legs, letting me know without words in no uncertain terms what I was to do.

She sighed as I pushed into her with her beneath me, and it was just as heavenly as I remembered from the night before. This time we went slowly, and I thrust in and out of her leisurely, taking the time to kiss her between thrusts. She was looking up at me with her beautiful blue eyes glazed with pleasure, her hair beneath us in a pool of gold lit by the sun.

She wrapped her legs around me and pulled me down to kiss her as we made love. I was slowly but surely driving her to her climax, as evidenced by the increasing pitch of her moans. I was thankful for that, because with those visuals and that pussy I wasn’t going to last forever.

She began rubbing her clit and I quickened my pace as I felt my orgasm building. We came together, her tightening up on me and squealing as I unloaded into her as deeply as I could. I dismounted and flopped beside her. We made out for a little while before she got up to take a shower. As she got up I could see some of my seed leaking down her thigh.

I got into the shower with her and we washed each other, but didn’t have sex. That was okay though, as I loved just fondling her marvelous breasts.

We got dressed, her putting on a spare uniform (“always be prepared,” she said to me with a wink). She gave me her number and kissed me deeply, pushing her tongue into my mouth. Then she left for the airport, and I left to check out and go to my work meeting.

We stayed in touch over phone and text, and had sex a few times when she was in town, but it eventually fizzled. Still, I always look back on this memory fondly as one of the hottest hookups I’ve had.

Source: reddit.com/r/gonewildstories/comments/4c6cv5/hooking_up_with_my_flight_attendant