Connecting Flight: I'm Dolly, Fly Me
Those old sexy stewardess stereotypes from the 1960’s and 1970’s seem so quaint, don’t they? The stewardesses in the movies and television commercials always look like models, the travel seems so glamorous. That whole image was revived by Steven Spielberg in the movie, “Catch Me If You Can,” with Tom Hanks and Leonardo DiCaprio. I love that movie. Now, the flight attendant, to use the term that was in vogue when I spent a couple years with USAir (now USAirways), in that movie who hooks up with Leo is played by Ellen Pompeo, the lead actress in Gray’s Anatomy. I have a few hookup stories of my own, but there was one particular hookup that I think of most often.
“I’m Dolly, Fly Me.” There really was an airline commercial in the 1970’s where the sexy stewardess says her name, and then, “Fly me.” I said it only in the crew lounge to one of my fellow flight attendants. She didn’t understand the reference. Oh well, we were both pretty young. I was 21 and taking a year off from college to see more of the country than I’d previously been exposed to, and the only reason I knew the line was that my mother had been a flight attendant before marrying my dad. No, they didn’t meet on a flight. A guy she met on a flight took her to one of his parties, and she always thanked her host for his hospitality. Dad said he knew he’d marry her as soon as he laid eyes on Mom. But I didn’t follow Mom’s path to being a flight attendant for the sex. It just worked out that way!
It was a late-night connection, and this guy was cute, flying alone. He couldn’t take his eyes off me; subtlety must be something guys learn when they get older. Not too many passengers on the flight from Philadelphia to Hartford that night. When I asked him what he’d like to drink, he paused and then said, “Coke, please.” Since there weren’t any other passengers in his row, I kidded with him and said ,“We’ve got something stronger. I won’t even card you since I’m just barely of age myself.” That got a smile from Mr. Never Took His Eyes Off My Body. I was flattered. I got leered at a lot, and often wore my grandmother’s engagement ring to try to reduce getting hit on, but I hadn’t worn it this night and he wasn’t creepy or old or fat. No, he was damn cute. “Ordinarily I’d love to, and to buy a round for a beautiful girl like you, too, but I’ve got a job interview tomorrow that’s pretty important. I’ll stick with the Coke, thanks.”
Was it sleazy of me to let my hand touch his more than I needed to when I gave him his drink? And I brought him the full can of Coke. Most flyers would interpret that as flirting from me. Let’s see about my college fella here, since I knew he liked looking at me. And why not have a little flirty fun? I was between boyfriends, and my couple of handsome fuck buddy pilots I knew hadn’t been successful in in bidding on the same routes I was flying lately. And then I surprised him, since he was in the last occupied row, and gestured toward the window, so he slid over. I sat in the aisle seat. You can only ever hope to get away with this on a late-night, lights-out flight that is scarcely filled. Not a ton of people beating down the doors to get to Hartford that night.
“So who’s your interview with tomorrow? Oh, I’m Dolly.” He shook my hand. I let it linger in his a little. “Ted.” Polite.
“Big insurance company. Junior finance position. I’m a business major. Doesn’t pay all that much, but its great experience. I hope I get it.”
This was an April flight. Getting toward the end of the academic year. “Do you have other offers?” I asked Ted.
“Not yet. This is pretty much my last shot to graduate with a job. God, I don’t want to graduate unemployed.”
“Well Ted, I’m sure you’ll do great, but if I spend any more time sitting here, I’ll be the one who is unemployed, so I’ll come back and check on you later, okay?” And I got up, smoothed my skirt, and winked when I looked back over my shoulder and saw that, yes, while drinking his Coke, he was stealing a glance at my ass.
Now, I’m a runner, played tennis in high school, and had always been active in sports. Back in my college days, I was a spry, flexible, horny little girl with a firm body and no reason not to go after what I wanted. I liked sex since the first time, when I was 17. So, by the time I was flying for USAirways, I’d been fucking for four years, and I’d learned some real skills. I wasn’t shy, I wasn’t self-conscious, and, since I was the one in uniform, I always felt in control on a plane. Cute guy wants to look at my ass? I’m just sorry I’m in this polyester uniform, that’s all. He was fuckable, and the feeling appeared to be mutual.
I made sure to place a hand on his shoulder when I stopped back by to pick up his empty can and cup. I dragged my nails on his shirt as I walked away. Okay, that was pretty slutty for a professional flight attendant, I’ll admit. A girl’s gotta have some fun, though. And this was much more innocent than the political convention in Boston. Freaking politician or lobbyist or whatever he was, he was smooth, didn’t have anything smaller than $50’s and $100’s in his wallet, and I had an extra 12 hours of layover the next day. So I really could go out and drink and screw men that night without any impact on my employment. Oh, I could see where he’d slipped his wedding ring off … so what?!. The guy invited me to an important as hell party at the Copley Plaza, only one of the fanciest, most important business hotels in Boston. I ate lobster tails, drank champagne, had sex with a congressman, and Mr. Lobbyist put thirty--THIRTY!!--$100 bills into an envelope and said he hoped I’d had a good time and I should buy myself something nice, whatever I wanted, that it was just a gift, that’s all, and had nothing to do with the congressman. I didn’t think this college boy had any Benjamin’s for me, but then I enjoyed sex both for my own personal choosing and the excitement of sometimes knowing that there was a very nice, generous present to be had for enjoying myself.
I had simply considered that it was fun and innocent to flirt with Interview Boy when I completed the end-of-line checklist and close-out on board, and then got onto the hotel shuttle to the Hilton with the crew. No sex with these pilots, and my fellow flight attendant was a Bible thumper, so she wasn’t going to be any fun. Crew got on, and then the shuttle went around to baggage claim to gather some civilians. A short guy with gray hair got on, and then--HEY!!--My Interview Boy!
Ted got on, and I saw his face light up when he saw me. I suspect I looked the same. I motioned toward the seat next to me, and then, still being the flight attendant that I was, I helped him slide his valet bag, carrying his interview suit, no doubt, onto the luggage rack. “Welcome to the Hilton shuttle, Ted!” “Hello again to you too, Dolly. What a coincidence. So this is where y’all stay in Hartford?” “Yeah, they take pretty good care of us. Used to get stuck at airport hotels, but there was nothing near here, and we fought for downtown hotels near stores and restaurants, because we need to shop and get a decent meal, since a lot of us will fly for most of the business week.”
It was about a 20-minute ride. We didn’t talk much, but I told him a bit about the hotel and what was nearby, and he again told me he wasn’t going to go out. He’d connected in Philadelphia, so he’d been flying a while, hoped he’d be able to get some dinner. We looked at our watches, and I told him that room service was (in those days, anyway) available until midnight, or there was a lounge downstairs with a bar food menu. “We go there a lot when we don’t have early flights the next day. Think I’ll go there tonight.” And then I just didn’t say anything more, wanted to see what Ted did, or didn’t do. I was making it clear I would be in the mix, and wanted to see if he had any interest. “Pretty early car service tomorrow, important interview.” “Sure, probably the right thing to do. Won’t be the first plate of chicken fingers I ate alone watching a hockey game in a hotel bar.” That was bitchy of me! But his cock twitched, I noticed, and he was definitely thinking about it.
The airline had a big corporate account, so we were always met in the lobby by a concierge, and we were each handed folders with our room keys and meal vouchers. When the concierge gave me mine, he absent-mindedly said out loud, “Miss Jewel, you’re in 1115.” “Thanks, now all the sex criminals know where to find the young blonde stewardess” was what I wanted to say, but I let it go and just thanked him. I said to Miss Bible-thumper, “I’ll be down in the Fern Bar in 15 if you want to meet?” but her reply was, “Scriptures and sleep for me.” I thought it was hilarious three months later when the scandal broke that she’d gotten pregnant with a married pilot and he denied the baby was his, because she’d been bedding down a half dozen pilots. But on that night, I thought I was the flirty, slutty one, relatively speaking.
Hartford was a hockey town in those days, and in the spring it was Stanley Cup playoff time. I liked hockey. The guys always had great legs when you met them, they were mostly aggressive as hell, so the sex was rollicking, and the hitting and fighting was a great release. And, lo and behold, Hartford knocked off the mighty Montreal Canadiens that night in a first-round game! I was so into the game, I almost didn’t hear Ted ask me if I was with anyone or could he join me at my little table. I was so happy to see him, and, truth be told, it made me a little wet. Ted ordered a burger, fries, and another Coke. I teased him that he was going to be unable to sleep with all that late-night caffeine. “I’ll sleep,” was all he said. Shit, Teddy, I’m practically giving you every opening, and you’re really not going to accept the offer? I’ll offer my pussy up as an easy lay to a nice, cute, polite boy. I like to be fucked hard and deep by a stud. Or some combination of those if I need to. But I won’t beg to be fucked deep and hard; a girl who looked like I do shouldn’t have to. Ted looked in my eyes and asked me all sorts of polite first-date type questions. I said to him, “Ted, I’m up in room 1115. Did you want to see what the view is like from the 11th floor?”
And little interview boy put his hand on mine and said, “Dolly, I’m going to wish I did for the rest of my life, but if I took you up on your offer, I suspect I wouldn’t sleep much tonight and I just need to be ready to have a great interview, instead of smiling and exhausted with all my brains scrambled from time with a sexy lady.” I hate to be turned down, but hell, that was about as polite and charming a way to do it as I could think of. We both stood, and gave him a hug, making sure to press my tits into him, and let him smell my perfume as I gave him a face full of my neck and hair, and told him, ”Good night.” When I got back upstairs and used my vibrator on myself that night, I thought of taking Ted’s interview suit off of him and then fucking him oh so good. Damn, he turned me down!
The next day I had short flights to Boston, then Syracuse, then Providence, then Albany, and then the duty day ended back in Philly. I changed into a pair of jeans, red, tight, kinda fun and sexy, but within regulations, and a pullover sweater and heels. I’d deadhead home to National Airport, now called Reagan National, and take the Metro out to Arlington, where I shared an apartment. And, what to my wondering eyes did appear, but an interview-suited Ted, walking up to my deadhead gate. “Dolly!” he said. “Ted!” I hugged him. I was really happy to see him. I was happy I could remember his name, and it was hot that he remembered mine. Not like I hadn’t ever forgotten a guy’s name in 24 hours. Though most guys remembered Dolly and tried to ask me out, Ted hadn’t hesitated. He knew exactly who I was. I held the embrace, so that I was just leaning back, our arms still around each other, like old friends, and I asked him, “How’d it go?” “Pretty well, I think, they lengthened my day, changed my flight to add a couple of extra interviewers to my day.” “So that means they like you? Of course, right?” What the hell did I know about corporate interviewing? So where are you going to?
“Back to school. I go to G.W. You know, George Washington. In D.C.”
Well, fuck my pussy full of college-boy spunk! Cutie boy lived in my city! “You’re on the 8:30?” “Yes, how did you know? Where are you going?” “I’m on the same flight. Ted, I live in Arlington. I can’t believe I never saw you in the airport before!” This had me so psyched!
“I really don’t fly much. Take the train from Union Station, so you wouldn’t have seen me. It’s not as if I’m a frequent flyer.”
This time I took his ticket from his hand, went up to the gate agent, whom I knew, and asked her if she could seat us together even though I was a dead-head and wasn’t supposed to get a seat until everyone else was assigned. I think Teri, the gate agent, had met a few horny flight attendants in her day. She smiled, said nothing, worked some magic with the computer, and had us in D and F in the front row of coach, with extra legroom with the bulkhead seats, on the side of the aisle with just the two seats. Ted wasn’t complaining.
We settled into our seats, and I confess I had lust in my loins. Nice guy, cute, single, seems to have prospects for a good job, what’s not to like? Sure, I thought, he probably doesn’t have any money at the time, but that was kind of secondary. And temporary. I’d learned that the older guys who were interested in private time with me were separated into two categories: (1) the generous ones who understood there was significant value to an evening of intimate pleasure with a young, fit, attractive blonde who was sexually open to adventure and enjoyed pleasing a man and having him please me—and who was capable of being discreet and not letting the wife find out, and (2) the jokers who just thought I was going to fuck for a couple drinks. Uh, no! Ted, I assumed, knew none of this, and to him I was a girl his own age who had caught his eye and returned the interest. Sometimes making love is a nice change of pace from fuck-a-thons. Not that I’d complain if I discovered Ted had a young talent for eating pussy. Usually that skill wasn’t refined until a guy was into his 30’s, but I’m not complaining.
Scored a couple of complimentary drinks with some coupons I always carry. Had to hand them to Ted, I’m not allowed to use them for personal use. But he could use them as he pleased. So a little vodka toast sealed our little small talk and—hello, romance--hand holding in our little world of bulkhead seats 10 D and F. They always start Coach with row 10, even if First Class or Business Class only has four rows. Go figure!
I was really soaking my little cotton bikini panties. Hadn’t realized I was going to be meeting a boy for a “date” on the flight, not that my outerwear could have been flashier. Deadhead dress rules governed me on the flight, and my tight pants were on the edge of compliance with those. I had been told by lovers, professional and personal, that I taste great, and from my own second hand tastes, off a lover’s cock condom before taking it off, or off his fingers, or my fingers, or his mouth after he’s gone down on me (okay, or off her mouth after she’s gone down on me, as sometimes my play for generous gift dates included another sexy girl), I did think I tasted sexy. So, embarrassing as it might be to soak my cotton, I figured that would just be a sensual and erotic whiff of sex for him just before I felt his tongue trace my inner and outer layers, and then spread my juices over my clit …. Shit, I really wondered if I was going to make it out of the terminal before I insisted he fuck me but good.
Ted had a pretty decent tent in his trousers from his chubby. I definitely would have stroked it from the outside if not for the older couple in the row across from us. Not the biggest I’d ever mounted, but looked like it would feel good. “So you didn’t need to rush right back to campus, did you Ted?” Fast smile and response, “I’ve got time when we get back. Want to do something together?” Oh Ted, really now, was that the best he had? “I know a great place in Arlington. Want to come?” And yes, I totally meant to say it that way. I may have been younger, but I was never shy. “I’m all yours,” he said, and squeezed my hand, which he still held in his. “Yes, you will be.”
I’d have sucked his tonsil’s out of his throat except that I really did respect my employer and the airport and its property, and any official licensed transport service on the property was an area where my conduct was subject to scrutiny. So since the cab or the Metro leave the airport, I still couldn’t give Ted a blowjob until we’d gotten out of the cab or off the Metro. A bar or restaurant or my apartment, sure. A private car, yes, but not a rental. And you thought the NCAA had byzantine rules for jocks taking benefits—my sex life was so damn regulated? See why I didn’t stay with the airline and make it a career?
I suggested we drop the bags at my apartment. I did kiss him, not a porn star kiss, a girlfriend kiss, when we exited the Metro station. I lived two blocks away from Ballston station. A nice apartment that my flight attendant pay wouldn’t have come close to covering. I had a gentleman friend whose think tank had a couple places for visiting speakers to stay in the comforts of a home rather than a hotel room. Since he and I started having a couple dates a month, one of those places was permanently listed as “occupied, Chairman” on the records. I’ve been called a lot of things, but that was the only time I was called “Chairman”! LOL, I swear, the shit that goes on in Washington!
We dropped our bags and Ted’s jaw dropped. “Nice place …,” he managed to say, looking around. Okay, this was a $1,000,000 executive place, designer furnished. “My daddy pays for this.” That seemed to reassure him. I’d been careful to say “daddy”, and I didn’t mean to imply my FATHER was paying for it. I personally don’t have a fetish for wanting to fuck my own father, not that he isn’t handsome, but it was all just an adventure in fantasy, and if my date wanted me to call him daddy, and the think tank’s chairman did, I could do that and not crack up. A turn on to be fucking someone so damned kinky, don’t you think? Some other fantasies came true there, too – but every character in every fantasy was always at least 18 years old. I’ve got some standards!
I took Ted’s hands in mine, clasped our fingers together, and kissed him. The on-the-street kiss had been brief, girlfriend-like, a bit of tongue, nice. It meant, “I like the date we’re on.” This was deep, erotic, seductive, and I felt myself losing myself into the kiss, and felt his mouth coming alive. This kiss meant “Oh God I can’t wait to feel you inside me.”
I thought about taking him to the shower. For about a second. Then I tossed his suit jacket onto the coat rack, nipped at his neck and ears as I reached around his neck and shoulders to undo his tie, and tossed that toward the suit jacket. Then I lowered my target and undid his belt, unzipped his fly, and released that straining thick sausage I’d been admiring from the wrong side of his pants. Nice, thick, already hard, clean, not too veiny not too smooth. The kind I could ride, buck on, and enjoy the feel of the penetration. I kissed the tip, ran my tongue around this darkening head, stroked my fingers along the base of the shaft. “Oh God,” I heard Ted gasp. The first of many spiritual utterances that evening.
I pushed him toward the sectional couch. Lots of space for sex. I pulled my sweater over my head as I did a model-on-the-cat-walk strut over to him, and gave it my best unattainable-sexy-bitch-model face, narrowed eyes, fuck me if you dare look on my face. Reached behind me, undid my bra, tossed it to him. It landed next to him. Ted finished kicking off his shoes and dropping his trousers. I pulled his shirt off him, dragged my fingers down his chest, his nice abs, and then, on my knees, bare from the waist up, and clawed the inside of his thighs, pointed his twitching hard-on toward my lips, and lowered my head onto him, taking about half the shaft into my hot cock-sucking throat. Thrusting my tongue up and down the underside of his cock. Pre-cum already. But young guys my age always had multiple pops in them. No problem.
I moaned onto his cock, letting him feel the vibrations. My mouth in a tight “O” shaped, and pumped my head up and down on his cock, now stroking his swollen balls with the nails of my right hand, lightly gripping, targeting mostly, the base of his cock with my left hand. The one with grandma’s ring. He later told me he thought I was engaged and holding out on him. “So why did you let me suck your cock if you thought I was engaged?” I asked him. “It felt so damned good, and if you were engaged it sure wasn’t slowing you down any, so I figured maybe you were having second thoughts about the engagement and that I still had a shot to be your boyfriend.” Awww, that he still had a shot. He really did want me to be his girlfriend! While I found that sweet sentiment out later, at the time what I knew was that he was gasping, shaking from pleasure, thrusting his dick upwards into my unstoppable mouth. After maybe five minutes of oral, with some spitting onto his cock, some slutty slow hand strokes, and some “Mmm, I want to taste your hot cum in my mouth, Teddy,” I brought him to his first climax, as his hands finally found my breasts, kneading them, lightly twisting my nipples. I sucked him dry as his hands stiffened and stopped playing at the moment his cumming locked up his body. Didn’t spill a drop. I showed him his load in my mouth as he came down from his orgasm, then swallowed it. A peck on the lips, maybe I gave him back a swimmer or two, and I went and got us a couple glasses of water. Mouths rinsed, he kissed me, and his hands returned to my breasts. I whispered for him to really go at it with my nipples, how I loved feeling his hands on me. He also stroked my back, feeling my toned body. So glad I’d never given up fitness and running and working out. Heck, I loved to have my own hands on me, too, but definitely loved knowing my body was turning a guy (okay, or a hot girl) on as well. He was getting hard again. Already. I miss the days of fucking college-aged boys sometimes, but it’s a fair trade-off for the skills a grown man uses on me.
Now my jeans were so tight that I had to slip my fuck-me heels off to get the pants off, but I put them back on. I liked that when we were standing we were about the same height when I wore these heels. Ted sat me back down and took a turn giving oral. Nice, good beginner’s instincts. Between his eager tongue, his wandering hands, and a well-placed finger or two of my own, I was going to cum. I knew I was so ripe to be tasted and that my couple of hours of body self-lubrication made for a slick lick-fest. His hands held my firm, tight ass, as he let a finger tease my puckered ass hole. I love to have my ass fucked, and I was no anal virgin at the time, but this sweet lover was all about my pussy that night, and I was happy for him to stay where his first instincts guided him. I grabbed his hair and moved his head like a puppet, in the up and down movements I wanted, and some other rapid fire flittering, too, so that he knew how I liked it. “Taste me, lick it,” I told him. He didn’t need telling, I don’t think he ever heard me. I was smeared on his face, cheekbone to cheekbone. He put a couple of firm fingers in me while he licked my clit and I got to the finish line, as my moans and grunts dissolved into a relieved, all-out sigh and exhale. He leaned down to kiss me, to feed my pussy to me from his face, and I savored my body’s sexual taste from him. His cock was twitching up against my well soaked doo-dah again, and I loved the feel of his head sloshing across my wet zone. So close, oh God, how I did want that to penetrate me, be inside me, swell, and explode. I pumped my hips in his face and then pushed him back and took him to the shower. Off with the heels again, and in we went. Scrubbed each other’s body, embraced, sucked each other’s tongues, twiddled each other, and then I turned around and let him tease, but not penetrate, me with his cock head. Dang it, no condoms in the shower. He finger fucked me, deep inside, three fingers all grouped together, and then flicked my clit while pulling my hair and telling me how good he knew my pussy would feel to his cock. Damn right, I came!
I dragged him to the bed, still on an adrenaline high from our sexual connection--and emotional one, too. I mounted him cowgirl, facing him, after applying a condom. Nice to be back next to the nightstand. He’d cum earlier, so he was going to last. He made it through a pair of riding-his-cock-cowgirl style orgasms, and I bit down on his shoulder for the second one. I turned to face the same way as him, give his hands better access to my tits and my pussy, re-lowered myself onto his still hard powerful cock, and reverse cow-girled him to another orgasm for me. Then I knew he was so close, the way he was pleading with me to keep fucking him, how good my pussy felt. From a pure, raw sex standpoint, I’d have loved some doggie. But Ted had this intimate desire, so I turned over onto my back, and sure enough Teddy boy practically leaped at the chance to take me missionary. He was on his elbows, arms under me, clasped to my shoulders. Our kisses were totally in sync with each other, like we’d been fucking for years, not just a couple hours or so, with his knees spread to open my legs, and I spread them wide for him to bang away. He did, too, until he seemed to take the intensity up a notch and ordered me to wrap my legs around his ass and back of his thighs and pull him into me, hugging him with all four limbs at that point. If not for the condom, I’d like to think this depth of mutual lovemaking was how all children should be conceived. I guess it was romantic, maybe the most feeling I’d had from a lover up to that point in my life. The fun part was that since he was single, I could dig my nails in, not to be mean, just to be intense and to heighten the sexual connection. No one to get him in trouble with for having any marks of passion.
It was the second time I came that I remembered how I get such a great reaction from the boys when I voluntarily squeeze my pussy core muscle and feel his response in me while embracing me. That last one drained Ted, it was a lengthy cry of ecstasy, and he was spent. He stayed inside me, wrapped, until he eventually shrank enough to slide out. And that slide hit all of our hyper-sensitized nerve endings, too, and more cries of pleasure. He was graduating the next month, but that still left us plenty of time to get to know each other. And we did. And I started bidding more schedules that included Hartford once he got the job offer.
Fictional fantasy for your reading pleasure...ENJOY!