People Watching, Airports, The Rocky Horror Picture Show, Babysitting, Maui-- no tourists were harmed in the making of this blog

I love to people watch when I travel.  I sometimes wonder about their home lives, or what their travel plans include, or if I've just had a super terrific wild hot last sex romp on a trip (or just prior to a trip), I might imagine the dirtiest, kinkiest secrets my fellow travelers might be hiding.  You know, after all, I'm Dolly Jewel and I'm traveling in the same airport, or even on the same plane, and I've likely been doing some hot stuff.


Though this one pair, I just thought they were incredibly sexy, for sure I thought they had to be Mr. & Mrs. Gorgeous Models, and then in the priority boarding line I see them pass a smart phone back and forth and say things like, "now dad wants to talk to you" or "yes, mom, we'll always be your babies, yada yada yada, deal with it, your kids have grown up, okay?".  Wow, those two hotties were brother and sister?  So, did I regret my moments-earlier mental images of what this fitness trainer physique pair would have look like buck naked, her leaning back on her elbows, knees up and spread, heels hooked behind this tiny, gotta be hard as steel ass while he pistoned a potent, manscaped cock into her smooth fertile pussy until he came, while she gasped into his mouth between kisses, their perfect features looking like the hot weather girl and the too pretty for his own good anchor man....she had that great combination of a medium glowing tan with red hair and green, almost hazel eyes, while he had classic medium brown hair, not a single strand out of place, and a brighter green eye color.  Oh yes, I'd mentally stripped off the shorts and polo shirt from him, with the banded sleeves so his biceps looked even bigger, and she was just lean and sexy and fit, sculpted triceps, an ass that made me wish I had my own cock so that I could be the one to fuck her, and tits that had not yet even realized that one day they might sag.  No, I didn't regret those mental images.  I wasn't DOING anything taboo.  I didn't go out of my way to wish anybody was doing anything taboo.  Just two sexy people, imagining them fucking, that's all.  Oh, they turned out to be siblings?  Does that mean they could charge me extra to watch them, seeing as it was a taboo show and not just hot sex?  Well, if so, then please, let me get out my Black Card and charge the extra fee.


I love the idea of sexy bodies, and if they're breeding, mmmm, so much the better.


Don't get too worked up, I'm still Miss Safe.  Nobody goes plunging into my warm sexy snug welcoming sea without a proper diving suit.


They sat back in coach, that was a bummer.  I wanted to catch glimpses of them.  Who knows, maybe they even really do what I imagine.  Maybe they'd like what they saw if they saw me.


Okay, that last line makes me laugh.  I completely dress down when I travel.  Cap, hair up, large sun glasses, no makeup, cleavage put away....


Did you know, by the way that there is a big oversized lavatory on a Delta 777 in first class, on the right hand side as you face forward, opposite side of the plane from where the passengers board, that is amazing for mile high club sex?  A shame the sexy siblings were just on a mundane 737.  I hate screwing in standard airline lavatories.  Well, I don't hate it, its still sex that I've chosen to want.  Just can't get into all the positions I might want to experience.


Wait, was that....I could swear I used to play tennis matches against her on the tour, in the early days when I was still working on getting a ranking.  Some country that ends in "ova".  you know, like, "ova there, she's from ova there across the Atlantic..."  Bad joke.  Decent backhand, if that's her.  If she's the one I'm thinking of, she was screwing more than one player on the men's tour.  Always wanted to party with her.  I should linger when we get off the plane when we've landed back at FLL. 


This is Spring Break time of year.  So I see hot college students, as well as wealthy families, and some pasty, pale, in dire need of sleep and sun college students who are probably the future 1% type successful people because they look like they've been inside, working, all semester.  If only I knew which ones would make the most money in the future, I'd seduce those young folks.


And then there are the ones traveling with a nanny.  Too many designer labels on the luggage.  Everything designer.  Trophy wives, and inattentive husbands spending way too much time staring at their phones instead of their family.


I remember when I wasn't a nanny, but I was a babysitter and got a free trip to Hawaii out of it.  I finished college exams by December 16th, and then had a Jan. Term, where you go back and take one bullshit class for a week in January, pass fail, something of interest but in a broadening, liberal arts sort of a way, not something in my major.  Which gave me enough time to get in some babysitting before Christmas with a family I'd sat for during high school.  Let's call them the Smiths. So Charlie Smith and Debbie Smith had two children, and for fun lets call them Kenny and Barbie.  See what I did there?  The kids were ten and eight.  A fun age.  Because the hormones aren't raging yet.  Four years later I know Kenny was whacking off while thinking about me.  heard him mumble my name when I accidentally walked in on that show.  He was fourteen.  Not happening, good God, still a child.


But at ten he was still a cutie, a sweetie pie, and Barbie was a doll at eight.  And their parents, you remember Ken and Barbie.  Well, Kenny.  Anyway, the parents asked me would I take my babysitting services on the road with them.  To Maui.  For a week.  All expenses paid, spending money, and a thousand bucks when we got back to help with college spending money for the semester.  Hell yeah I was going!


So I got a free first class flight to Hawaii and my own bungalow at the resort in exchange for about five or six hours of child supervision sometime between 8 am and 5:30 p.m. on four days, and then three nights during the week I'd stay in with the kids from after dinner until whenever.  That left a whole lot of time for me to do my thing, day or night.  And the Smiths were cool.


I know what you're thinking, so, Dolly, which night did Kenny REALLY get his thousand dollars worth out of you?


Get your mind out of the gutter, dear readers.


I didn't fuck Kenny Smith.  Not that trip, not that year.  I'd fucked him during my last year of high school, when I came out of the Rocky Horror Picture Show at just before 2:00 a.m., since they only show the movie at midnight on a Friday night, and I went with a couple of my closest friends from high school, and there was Kenny, what the hell was a mature adult doing at the Rocky Horror show I wondered until I saw that he wasn't with Barbie. 


"Hey Mr. Smith, hi, its me, Dolly!"


I knew he was busted but I just played stupid.  Never know when having some leverage might turn into a Get out of Jail Free card.

He awkwardly introduced me to Brooke, his client, he claimed, who mentioned that she'd never seen the Rocky Horror show but had gotten interested after seeing an anniversary interview with Meatloaf and Susan Sarandon on Good Morning America.  "um, yeah" she chimed in.


Brooke was early twenties, pretty, wearing body glitter at night which is less odd than you might think considering we were in South Florida, and it was easy to see why a married dude would want to fuck her.  I was not quite fucking married dudes, and I was just a couple years younger than her, and while she was skankier than I could ever be, I wondered if she was a pro or not.  Like did he know Brooke's last name.  Or was that her real name.


I just let it go, and said it was great to meet her, and great to see him, and maybe I'd see him at the Rocky Horror Show again the next month, since that's when I was coming back, now that I knew he was also a fan.  Not that I was a fan, but I'm into a variety of interesting people-watching centered experiences. (Like, years later, imagining brothers and sisters on my flight from LGA to FLL having hot sex).


So three days later Kenny Smith stops by while walking his dogs.  They must have been her dogs, I hoped, they looked way too yappy and frou frou to be a man's dogs.  And he knocks on the door, seemed relieved I answered and not my folks, and thanks me for my discretion.  That she wasn't so much as a client as a friend going through a tough time.  I just smiled, and simply said, "It's cool, Mr. Smith, I'm not a virgin, and I don't tell things that aren't my things to tell.  Would it be safer for you if I was your next date for a movie, though?"


His shorts throbbed.  I'd guessed right, my hope that he'd turn out to be interested.


"Not just pretty, but smart, too, Dolly.  What movie are we seeing?"


Oh this was too easy.


"Let's do the time warp again.  I'll meet you at the theater, the line shouldn't be too bad if we get there at eleven, and they let us in at eleven thirty."


I dressed in costume this time.  Slutty torn stockings, garters, stripper heels, bustier... God bless the Rocky Horror Picture Show, where else is looking like a cheap street walker ever something a girl from a good family can do and get away with?  Dad rolled his eyes, but mom gave him a playful smack, she'd seen the movie and understood the context, and said that she'd explain it to him later and handed me twenty dollars and told me to have a good time.  So cool, my mom.


A few years later she confessed she'd had her best sex with my dad in years less than half an hour after I left.  I'd like to think it was the spirit of the thing, the movie, the clothes, and not me.  Susan Sarandon in a half slip at the age of twenty five is all the inspiration anyone could need to fuck at the thought of the Rocky Horror Show.


Kenny's eyes totally bugged out when he was me. I hooked my arm in his, pulled him close, and said, 'Meatloaf for dinner again?"  He raised his eyebrows.  "Its a line from the movie? Hello?"


Turned out he hadn't watched much the last time, with Brooke.  She'd picked it, he confessed.


When the lights went low I slid my hand to his crotch, and he was paralyzed.  "Truth or Dare, Mr. Smith." I said, and he whispered, very unsurely, "Truth?"


"Was Brooke an escort?"


He paused.  I had my answer.  "Its not that simple, Dolly...."  I thought that was so hot!


"Its cool, Mr. Smith, again, I know how to keep private stuff private."  then I cupped his package in my hand, and his nice sized tool throbbed.  "i'll save you some cash tonight, and I'll bet I can make you hotter than she could."


Throb, throb, throb.  Hard as steel now.


I don't want to break my promise of privacy to Mr. Smith.  At least not more than you can already guess.  I licked my own hand clean after I induced a manual climax from his baby-fertilizer, and then I licked his fingers and tasted myself after I pulled his hand into my own crotchless panties.


And the backseat of the big Lexus sedan is plenty good for fucking behind the high school gym.  Fanciest car there.  Only underclass sluts fuck in Camaros.  I hadn't been laid in a Camaro in like a year and a half, I thought as Mr. Smith was inside me.


How young was I?  Young and naïve enough to think that it was acceptable to say, "its okay, I'm on the pill."  Again, Mr. Smith being a cool neighbor, said, "that's not being safe, Dolly, let me put this on."


"Oh, Mr. Smith, you feel so big inside me, oh fuck, I love how you feel up in me, I wish I could feel you cum in me... it would be so hot....."

"No, Dolly, we can't, this is plenty hot, you're so young and sexy, and your Rocky Horror slut outfit has been making me hard all night...."

"Mmmm, yes, like that, Mr. Smith, fuck me hard like Dr. Frank N Furter did to Janet, fuck me, oh God, I'm cumming, you're making me cum...."


And now you've heard about the first time Dolly squirted.


Regular sex is amazing.  Add something naughtier or forbidden about it, and now I'm gushing my sex juice.  I had no idea I could do that.  I've been so grateful to Mr. Smith ever since, for being such a great exciting fuck and pushing me over the edge to discover squirting.


And thankfully Daddy was out like a light from his amazing sex with mom so he didn't hear me come back in at 3:45 a.m.


But while there were other Kenny Smith sex evenings, none of them were in Hawaii.  The Smiths had a clean, wholesome family vacation in Maui, and added a third child nine months later.  Like I mentioned, they requested my babysitting services  after dinner for about half the trip.  So we've got the magic night narrowed down somewhat.


I'm assuming it was when I was doing my babysitting.  In my bungalow.


Unless they found someone else to distract or occupy the kids on my nights on my own.


Did you know that Californians pop over to Maui for weekends like New Yorkers hop on down to Miami?


So there was this guy from Manhattan Beach.  He was a fifth wheel.  Two couple and him.  And they called me over to the hot tub.  Something about, "we ordered too many Margaritas, we hope you're twenty one, we'd hate for this to go to waste!"


Not a bad pickup line, considering the guy who called that line over to me was one of the two coupled-up guys.  Todd was the one without a date.  'She got sick, was hacking and coughing, and didn't make the trip."  He was cute, he had freckles.  I don't know, like a lost puppy.


I sipped the drink.  "I prefer the frozen ones." I said,  I thought it sounded grown up.  Ha!  Oh, to be twenty-one again.  Old enough to realize that when I was eighteen I had been irresponsible to beg Kenny to fuck me bareback, but young enough to think a frozen douchebag tourist drink was mature."


Todd never pushed a drink on me.  Never got defensive when I asked how he could leave his girlfriend home sick and go on the trip without her, he just said, she wasn't his girlfriend, and he'd never been to Hawaii and didn't want to miss it.


I liked that he wasn't being a schmuck and trying to impress me or get me drunk or bragging about his money or car or house or plane like the guys with the dates. No wedding rings anywhere to be found.  So much later, the second time I spent an evening with this crew at our same resort, I figured out about extended escort travel companionship dates when one of the ladies and I excused ourselves to go to the ladies room and I asked how long they'd been dating and that her date didn't seem to know much about her.  'Um, we date, but we're not exclusive, its kind of an arrangement, you know what I mean, honey?"  He was a friend, but she had a lot of friends, and until some of her auditions turned into parts and bigger roles, it was helpful for her to have generous friends.  That sort of thing.


No, I never ever confided anything like that to some college coed while on a Dolly date.  That was my impression at the time, "I can't believe she just told me that.  I was a better, more discreet lover for Mr. Smith when I was still in high school and promised to keep his secrets than this girl, and she just got a trip to Hawaii and paid for her sex.  Kenny never paid me for sex.  It was just cool to get to fuck an experienced, handsome married man, and now it had earned me the same trip as this girl.  Except I'd flown first class all the way from Florida and had time to myself, and it was a cool trip and Kenny and Barbie's kids were still sweet, and ..... my future marketing plans learned some lessons from the actress from LA.  Some what not to do lessons.


And Todd?  That first night I'd thought he was into me and then I got left when he abruptly said, "I hope i see you again this weekend, I need to go now, though."  But then he made it up to me two night later when we all got together again, and that was a special night.  He made staying up all night and then seeing the sun rise from the top of Mount Haleakala sound really cool, and then it was fucking freezing up there before dawn, oh my God, way below freezing on Hawaii, who knew that was possible, and then we came down the mountain and he brought me back to my bungalow and I still needed to warm up and I took him by the hand and said to take a shower with me to help me get warm. The shower was kissing, my stroking his tool, him feeling my boobs, then twiddling my clit, and then we were about half toweled off when he made love to me in the bed. Yes, I said "made love", it was gentle and caring, and he didn't go nuts.  Funny how what might come across as a boring, routine lay if we'd been married and doing nothing else for ten years can be so wonderful with a first time, and I realize probably only time, bed mate.  it made Maui a special memory, I learned a lot, came, yes, I gushed and squirted but that time it was because I worked my mind to want him to experience that with me so it was a first kind of learning sexual experience for me again, only associated with Kenny in a tangential way only.


I totally zonked out and fell asleep watching the kids the next day.  Sitting in my chair while they wove grass and bamboo into souvenirs at some hand-on experience thing for tourists.  So I didn't bring back anything I'd made, I bought something in the gift shop.


A half dozen years after, at a New Year's Party in my parents neighborhood that I went back over and attended, I saw Barbie and Ken again.  I thought something was odd, and Barbie was not talking to me and I'd always remembered her being friendly, and always brought up Hawaii.  Did she know something?  Was my past going to haunt me?  What, did she for some reason think I'd screwed her husband on Maui?  Imagine that, for all the times I'd borrowed Kenny to fuck me, I was going to get blamed for fucking him on an occasion when I hadn't done anything with him.


Then Barbie got next to me and asked me to accompany her to the ladies room.  Oh God, here it comes. 


"Dolly," said to me, "You remember, Hawaii, of course, right?"


"Sure, Mrs. Smith, " I replied.


"You're a bit too old for that Mrs. Smith, now, Dolly."


'Okay, Barbie."  I was nervous as hell.


"Well, I wonder if you could occupy Kenny and keep him here at the party, dear.  I hope you won't be insulted but let me give you this gift to show you that I value your time, “and she slipped what later proved to be five hundred dollars in folded Benjamin's into my hand.  "I'll need about two hours."


Confusion.  Relief?  Huh???  I guess my face showed all that.


"Look dear, its nothing illegal.  But an old friend from Hawaii, well, from California actually but I met him in Hawaii, on the trip with you as a matter of fact, contacted me, and he's in town for this one night, seeing as this year we've got that football team from California playing in the Orange Bowl.  Usually ever since Hawaii I've seen this friend when I travel to California, but well, you see, Kenny doesn't know about this friend and doesn't need to know about him.  Ever.  Understand, dear?"


In my relieved and suddenly sex-ignited head I said, "I understand more than you can imagine." But what I said out loud was, "It’s all good, Barbie, I'll figure out a way to keep Mr. Smith distracted, you can count on me."


She smiled.  A knowing smile.  "I'm glad, Dolly.  Todd says 'Hi' by the way, and wondered if you might want to see him again while he's in town, but I told him he still owed me for when he didn't show up for our second late night tryst in Maui which he later explained was when you took him into your bungalow.  Well, at least I'd gotten him the first night out there when he left you behind, but you really ARE tough for a man to ditch twice I suppose.  Anyway, no harm, I'm the one who came back from Hawaii pregnant, not you.  In case you ever wondered where our youngest got his freckles.  Oh don't look so shocked, Todd was payback for you seducing Kenny with the Rocky Horror Show, dear."


I was beyond shocked.


"Relax Dolly.  I've had so many hot nights with both Kenny and Todd hearing about you....if only I had the nerve to make love with a woman, I'd really want to sample what you have to offer, you sound amazing, but in the meantime, though, I'm taking Todd for a whirl and why don't you go slip away with Kenny so he can get me all hot and bothered later on telling me about it later on.


I'd have never imagined that story if I'd been looking at Barbie and Kenny and their older children and me getting onto the plane.  But it all happened.  You never know.  Hey, maybe you and I will be on a flight together, sometime.  Anybody want to take me to Hawaii?


Purely fictional fantasy for your reading pleasure!

< Return to my blog