Does Dolly Gamble

As touring trips go, the ones to New York City and then on to Connecticut are often so rewarding.  This last one was a great example.  After a non-stop flight into LaGuardia, I was met by the private car and driver of an extremely affluent client who took me to a fantastic suite provided by another client.  I love when the Manhattan part of the trip is a mix of my established friends and a couple of new friends.  New York has its own energygetting in my runs in Central Park; getting my favorite bottled water from a bustling bodega in Grand Central Station swarming with people from every country, every race, every occupation;getting treated to the most exclusive shopping on theEast Coast; and, of course, topping it all off with glorious Dolly Date sex!  The New York wit, edginess, and sense of humor are just sort of the dessert.


Sure, I love the excitement of New York, but the cultural diversity makes it fascinating.  This shouldn’t surprise youyou think I do all this and love it so without being a student of human nature? Take, for instance, one of my favorite Manhattan clients, Fielding Melish, a hedge fund attorney with a big law firm in a prominent office tower.  The man not only makes several million dollars a year as a lawyer to the most affluent financiers and investors in the world, but also knows wine vintages and labels from Austria to New Zealand and back again.  He was a national level polo player growing up, through college, and beyond, and still plays socially with an elite bunch (bless Fielding’s hearthe’s arranged some magnificent introductions for me through his polo network).  I pride myself on my level of fitness (if you’ve been my lover, this shouldn’t be news to you), but I do feel it only fairto give kudos to a polo player’s thighs.  Fielding could squeeze me with his in some intense positions, and his staying power was just off the chart. The beauty of his stamina was that he scheduled gloriously long dates—it took him that long to cum and, in the process, he got as close as any mortal man can to fulfilling my capacity for sex and erotic passion.  Fielding Melish is5’8” if you’re being generous with your height estimates, has very little hair left on top of his head, and, if he were a house, might be described as short on curb appeal.  Dolly isn’t about surface impressions.  Fielding takes lots of time with his mouth on me, reading my body’s reactions, and his cock takes me through a variety of positions and orgasms.  But this morning, as I sit down to type out this story while my overnight date snores through what I hope is a gloriously dream-filled recovery sleep from last evening’s sweaty sex, I’m not thinking about last night, or even about my polo player Fielding.  I’m thinking about a previous New York and Connecticut trip that taught me that life is indeed about the journey, not the destination.


I have a favorite client from Connecticut.  This story doesn’t involve himbut there’s a joke he tells that reminds me of the trip I’m going tdescribe  He told me that “Connecticut is an old Native American wordmeaning ‘that place between New York and Boston.’”One evening, I was riding the Metro North commuter rail out of Grand Central Station through Harlem, through the Bronx, past Westchester County’s old forested suburbs, and toward the quiet, old money of Greenwich.  I’ve learned to dress down when I travel, tie my hair up in a ponytail, and not attract attention.  But sometimes my body gets noticed, particularly in warmer weather when I just can’t hide in bulky coats.  The commuter train seats face each other on either end of the cars, a pair on each side.  This arrangement provides more leg room when the seat opposite you isn’t occupied, so I sit in these seats when I can.  And this time there was just one man sitting on the other side, so the two of us each had leg room directly across and eye candy (each other) on the diagonal.  He was as handsome on the outside as Fielding was not.  If he were half as good in bed as Fielding, he’d have been a dream date.  Three of my four Connecticut dates had already confirmed, but the first one, a man I’d met before and who favored late dates, had not yet checked in.  And Mr. Diagonal, who appeared to be in his early60s, with a full head of salt and pepper hair, pinstripe suit, Italian shoes, and coordinated pocket square and textured silk tie, was losing the battle to stay focused on the evening edition of the New York Times he’d picked up to read on the train.  He’d seen my calves and thighs in stretch pants, shifted his eyes upward to my sculpted arms (thank you again, yoga!), and then seemed to just decide he wasn’t going to pretend not to be looking.  Which, by the way, turns me on—a man with the courage of his convictions; he likes what he sees and isn’t shy about taking it all in.  Our eyes met a few times, and, yes, I do still blush.  


“I’d say I’m sorry for staring, but I’m not sorry at all.I’m just feeling lucky to have such a beautiful woman in such great shape sitting so close to me,” he said at last.  As opening lines go, that one was pretty good. “Well, thank you!  It’s nice to know my workouts are working,” I told him.  “Lucky me to have sat near a man who has such a way with words.”

“My name’s Ken.  I’m taking the train all the way out to the end of the line in New Haven, where I’m being picked up by a car from the Mohegan Sun casino.  They host me for blackjack once a monthI go out for24 hours, I take them about half the time, and they clean me out the other half. Considering that the odds of the game are designed to favor the house, breaking even means I’m beating the odds.  I like the excitement, and I appreciate the respect the casino gives me.  You ever gamble?”


Does Dolly gamble?  How many different ways could I analyze that question?  I kept playing the game.  “I’ve been to casinos, though never the ones in Connecticut, if that’s what you’re asking.  And my name is Dolly.”  His eyes were brownwarm, assuring.  Nice hands, well groomed, and he appeared to be fit, as much as I could tell through a suit while he was seated, that is.“Do you live in New York, Ken?”  “No, I have an office in the cityI usually go in 3-4 days a week, travel a day or two, but I commute in from Darien.  Noroton Heights, actually.  But today I’ll ride the train past Noroton all the way to New Haven.  You’re not from around here.”


“Did my accent give me away?”  He laughed.  “Well, I meant I can tell you don’t live around here NOW, never mind that you have an accent that lets me know you’re not a native New Yorker or a New Englander.  No, you have too much tan without make-up or jewelry to be from this neck of the woods.  Plenty of tans to be found here, but yours is real, from being outdoors, not from a salon.  Florida or California?”


“You’re very insightful.  Florida.  What else can you tell about me?”  I knew he wasn’t going to guess my real story.


When you got into your seat, I noticed you’re traveling light, you’re in fantastic shape, and there’s no 10-K or half marathon in Connecticut this weekend, at least nothing big enough that anyone would travel in from Florida for, so this is a trip to see a friend, someone you know well, since you don’t have the right kind of luggage for any formal dress clothes.  No wedding ring, so perhaps a boyfriend?”  He was fishing with the boyfriend line, but his analysis was correct, though leading him in the wrong direction.  “Not a boyfriend, but you’re a very observant man.”  A silent pause.  Does Dolly gamble?

“I was supposed to meet a friend in Stamford (I fibbed—but I wasn’t going to tell him Greenwich was my destination), but he’s been delayed, so I’m going to just stay in and see him tomorrow.”  Which, except for the fact that the friends I will be seeing tomorrow are not the same man I would have seen that evening, wassomewhat true.  So Ken knows I’ve got no plans for the evening.


“I try to be observant, yes.  In blackjack, I have to remember how many face cards I’ve seen.  In poker, I have to read people’s faces, knowing what their cards are by the way their eyes look.  A beautiful woman like you shouldn’t have to sit alone in a hotel room this evening.  They have a Bobby Flay restaurant at the Mohegan Sun with a shellfish tower that is excellent and great wine pairings.  May I invite you to ride the train a bit farther tonight and join me?


Does Dolly gamble?


I hadn’t answered yet when Ken said, “Great, and thank you.”  He saw my surprise and told me that my smile said it all.  So I said, “Well, you are indeed very observant, Ken.  I’d love to.”


I could describe the dinner, the magnificent casino, or the small talk in the town car from the rather dingy New Haven train station to the glamorous casino in the middle of nowhere.  But none of those was the highlight of the evening.

Ken was a great kisser.  His lips were supple, soft, exploring, and knowing.  His tongue had a confidence all its own.  I’d wanted to shower and change, but Ken told me he could tell I really wanted him to ravish me as I was.  He was right again. He kissed my body as he uncovered it, my clothes tossed over onto a settee in the corner of his suite. His hands were deliberate.  My nipples never need much to harden in the first place, but a skilled lover’s touch will make diamond cutters out of Dolly’s nips.  His tongue circled my nipples and sent a chill up my spine.  I loved the visual of my fire engine red manicure running through that light, mature gray hair of his.  His body was firm.  Sure, there weresome signs of his age, but clearly he exercised and ate right. When we were down to just his knit boxers and my black Victoria’s Secret thong, our hands exploring each other, me feeling how hard he was as I reached down into his boxers and felt that slick smear ofprecum, and him slipping his fingers into my wetness.  was really loving the gamble I’d made.

Ken’s fingers found my spot and felt me quiver when he touched me.  His cock twitched with triumph as he got that reaction out of me. Did I mention he could kiss?  We prepared to start in missionary position.  Ken, being a gentleman, asked if he needed to run downstairs to get condoms.  I told him that I was a grown, responsible woman as I jumped up to grab one from my bag.


I was careful that he didn’t see how many I’d brought (hey, it was a Dolly tourmy wonderful men know how much latex I need for those trips!).  He was strongand had a wonderful feeling body, but, unlike FieldingMelish, he wasn’t particularly leg strong.  I wrapped mine around his hips and, with my hands on his ass,regulated his rhythm.  He nuzzled my neck.  Mmmmm, that’s so romantic and sweet.  We rolled, still attached, so that I was on top, and I leaned back. Ken’s handswere on my breasts, and I reached down and twiddled my clitty while rising and pounding down on Ken’s cock.  I saw his eyes rolling back in his head, so Iasked him if he was close.  He grunted out an “Uh-huh,” and I asked if I could wear it.  The flash in his brown eyes told me all I needed to know.  I dismounted, pulled off his condom, and worked him close to the finish with my mouth.  I pulled his cock out when his head snapped back and his eyes shut, and I smoothly jerked his pulsating cock in front of me, so that my tits were covered with a glistening sticky coating of his spunk. And then a first for me—that dear man hopped up a moment later and brought ME a warm, wet washcloth and cleaned ME up from thethick cum that he had gleefully pumped all over my tits.


We drifted off to sleep, but I awoke at 1 a.m. to the sensation of his fingers teasing my pussy and my body responding to his touch.  I rolled onto my belly.  He lifted my hips and I felt his fingers work my body into a frothy, slutty, wanton mess, while his other handgrabbed one of the condoms I’d broken out the night before.  In the dull light creeping in from outside, the drapes not being fully closed, Ken entered me, grabbed my shoulders to pull me back onto his cock while he fucked forward and downward into me, hard, in control, giving me pleasure along the way, but at that pointreally just doing what felt good to him.  My pleasure was a pure bonus. He reached forward, clasped my fingers, and stretched my arms out as if Iwere his captive and he were fucking me for all I was worth (a lot, LOL).  Ken could really screw!


To my surprise, Ken then led me to the shower where we kissed and fondled and soaped (and, well, maybe my mouth spent a little time wrapped around his cock).

Having had our shower fun, we dressed and went downstairs to the main casino.  Continuing with the incredible luck of the evening so far, at the VIP table playing $1,000 a hand, Ken was up $42,000 when I told him I needed to get a little shut-eye before heading back to the train and to Stamford (still lying about Greenwich, where I’d checked into my hotel via my phone, so I knew my room was still waiting for that day’s incalls).  At around 6:30 a.m., after a couple ofhours sleep and a kinky, kinda nasty sixty-nine with both of us tasting a good amount of our own flavors from each other’s sex parts, I jumped in the shower.  When I emerged from the bathroom, Ken was placing an envelope from the hotel’s desk into my bag.  “Just what are you doing?” I asked.


“You brought me luck, Dolly, so I thought it only right I give you 20 percent of last night’s winnings.  Well, plus a bit extra for a cab at the other end of your train ride, not to mention the unused hotel room last night,and whatever else you might need to make yourself ready to meet your friend.”  I thought $8,400 was a pretty good rate for the 10 or so hours I was with Ken, even though Ken was clearly a pick-up and not a client. A few minutes later, we took his town car to the train station, where I didn’t let him walk me in, kissing him good-by and thanking him sincerely for a wonderful evening.  Ahh, wealthy and classy silver foxes  .


When I got to Greenwich, as I checked in, I thumbed through the envelope from Ken and found a note. “I wasn’t entirely truthful with you, Dolly. Your no-show last night is a friend of mine, and he has been thrilling me with stories about you and showing me your reviews, including the one he wrote, for many months.  When he told me that he would have to cancel your date last night, I asked if there was some way I could meet you instead?  So that no-show shouldn’t be considered a no-show.  He’ll email you today, but this was just our plan for me to spot you in Grand Central, ride the train out, and try to pick you up so you’d just treat the sex as a civvie date, not a Dolly Date.  OMG, Dolly, I felt just like I was getting to live out one of those reviews I’ve read.  You’re obviously as hot when you don’t even know you’re on a Dolly Date as when you are intentionally trying to make it special for a client.  So, yes, I’m very observant, but its easier to be observant when I’d read close to 20 of your sexy reviews and those hot stories on your blog.”


Well thank you, Ken. Now you’re a part of my blog, too.


ENJOY! Purely fictional fantasy for your reading pleasure! 

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