Dolly Gets Steamy in Alaska

Cumming and squirting and thrashing and convulsing with pleasure, all with a spectacular view of Glacier Bay through the sliding glass door to our stateroom balcony.  Alaska was literally fucking amazing!


My Dolly date was with Burt, a lovely man, widowed, in his late 60s, who owned a successful chain of tire stores in his city.  He had a sense of humor and a comfortable easy-going nature, was balding and chubby in a cute way, and had been a perfect gentleman on our Dolly dates during the increasingly frequent visits he made to South Florida.  “Yes, Dolly, I AM coming here more frequently to see you.”   I wanted to make sure he wasn’t falling in love and hoping to have a non-Dolly date relationship.  “Not to worry, Dolly.  I just enjoy our visits, and I’d hoped to be traveling a lot at this stage of life, anyway.  Lucky me, I get to have special private time with you when I travel, is all.”  What a sweetheart!

And then Burt surprised me.  I guess I hadn’t realized just how many tires Burt had sold over the years, but on one date, just after I’d shown him his warm thick seed in my mouth before swallowing, he snuggled up to me, his post-cum cock pressed to my ass and deflating as we spooned, and asked, “Would you consider letting me hire you for a week-long cruise for a long Dolly date?”

Overnights or extended dates are for my closest, regular, most trusted friends only.  Burt had never done any overnights before, but he was plenty regular and trusted.  This was a week he was talking about. “Burt, you know I have to count all the time in the fee for any Dolly date.  Are you sure you want to ask me that?” He kissed my shoulder sweetly.  “Dolly, I’ve done the math.  Your webpage says 7,500 roses for the best 24 hours of my life.  So between getting out to Vancouver, taking the weekend to adjust to the time difference, the cruise, and then getting you back home, that would be 10 days.  Think of it as a very nice car I can buy for you instead of for me.  I already have a nice car, and I’m sure you do too, but thank you for looking out for me.  The question wasn’t “Can I afford it?” It was “Would you go?”  He kissed my arm, then playfully and gently nibbled a bit on my flesh.

I’d trust Burt to the Nth degree, but now he had me curious.  He totally surprised me when he said Vancouver—when he had said, “cruise,” I assumed he meant a cruise leaving from Miami or Fort Lauderdale (Port Everglades).  “Vancouver? Burt, are you asking me to go on an Alaskan cruise with you?”  He smiled a devilish and enticing grin.  “You catch on fast.  Smart and sexy, that’s my Dolly.”

My Dolly.  Well, I do sign my emails, “Let me be your Dolly.”  Hmmm.  Ten days of fully paid Dolly time and an Alaskan cruise.  “Burt, looks like we need to compare calendars, because that’s the loveliest offer I’ve had all week.  I’d love to go on a cruise with you.”

By now you’re looking for the sex part of this story, right, friends?  So I’ll skip over the logistics of what’s involved in the reservations and all that.  But I won’t leave out that, immediately after telling Burt I’d love to go on a cruise with him, I licked him back to full hardness, wrapped his cock, and rode him, leaning forward so he could feast on my nipples while my womanhood was filled, vacated, and then invaded again by this wonderful man’s cock.  Then I got on all fours with his hotel suite’s mirror at just the right angle, so we could watch his cock vanish in and out of me.  About the time we were both sweaty again, I reached for my toy (you know the one, 4 out of 5 dentists recommend this device, though not the way I’ve adapted it).  The vibrations of pleasure streamed through my body to his cock, and we came together and then collapsed in each other’s arms.  When he caught his breath, Burt told me, “This will be a dream cum true.” 

There were a ton of families on this cruise.  We teased about our cover story.  Should we tell people I was his wife?  Girlfriend?  Daughter?  (Nixed that idea quickly – I was pretty sure one of us would slip up and touch each other in a way that would seem affectionate to us but seem really creepy to someone who really did think Burt was my daddy).  We decided to do an only somewhat vaguely modified version of the truth—since the truth is always easiest to remember.  We tested it out the first night, when we checked in at the Four Seasons Vancouver after we met up in Seattle, me arriving there from South Florida and Burt from his home city, and took the quick connecting flight to a ridiculously clean, friendly, and beautiful city, Vancouver.  Our cover story went something like this:

“Welcome Mr. and Mrs. ______.”  The clerk’s voice trailed off when he noticed the disparity in our ages and the lack of wedding rings.  Yes, I have some terrific left ring finger ice I can wear if it fits the story line, but that wasn’t our story.

“Oh, we’re not married.  We’re just friends.  Really close friends.”  Mr. Clerk paused just a second until I winked as I flashed my Dolly smile.  Yeah, he was posing as my Sugar Daddy, and I posed as his Sugar Baby.  I’d thought about saying it differently, but Vancouver was just too magical of a place to use a harsh phrase like “fuck buddy,” the way Burt and I had rehearsed the script. 

The Four Seasons had wonderful views, a comfortable bed, and apparently sound-proof walls, because Burt really out-did himself that first night, though, with the time difference, I was glad we’d gone to dinner early, because we were both sexually spent and asleep by 9:00 p.m. Pacific Time.

Okay, a few logistics.  Before we left, Burt offered me cash up front for the gift, but toting that kind of currency ends up being illegal when you cross into Canada. We arranged discreet transfers in advance, but I did ask for a crisp $100 bill each day of the trip.  “So we can still feel naughty, Daddy,” I said to him, and he chuckled.  So our first morning, the sun came up very early--we felt as if we were still on Eastern time--right after he used his skilled fingers to work my fleshy labia and overly-sensitive clitoris into a frothy pond and then mounted me missionary.  It was so sexy to hear him grunt as he filled his condom while deep inside me, my legs over his shoulders, and say, “Fuck you’re hot.  Best hundred dollars I ever spent.  It’s on the nightstand.”  I hoped he meant it as a funny joke between lovers, and not a kinkier role play, because I laughed and slithered my tongue into his mouth while our bodies were still locked and embraced.

Now, the Blue Water Restaurant on our second night had some of the best fresh seafood I’d eaten anywhere—and remember Dolly is a world traveler.  We both were able to figure out which of the plethora of really hot women there were available to be hired for pleasure.  My time was already paid for, so that brunette, fit, fresh faced, mid-20’s green eyes, with great legs (everyone seems to walk everywhere in Vancouver, so it seemed as if all the women had great legs), was a really cost-effective threesome partner.  Mmmm, she was definitely Burt’s and my favorite Canadian food of the trip.  When Burt was in the bathroom, she placed my hand back between her legs as we lay nude in the sheets, told me she loved my touch, gave me a DFK, and asked me what my deal was, saying she knew I was a world-class pro.  I sucked her tongue and told her to Google Dolly Jewel when she got home.  I’m recruiting her to come to South Florida, where we hope to do some doubles soon.  With any luck, that can be during Burt’s next trip.

On board the ship, we turned heads everywhere we went.  Burt loved the attention of strangers, all the envious men seeing him arm in arm with me.  I loved bringing my favorite little black dress for formal night and a long form-fitting red number, the slit letting my legs attract some glances, for semi-formal night. Burt arranged a table for two, because we thought it would be a bit rude to introduce our consenting adult relationship onto someone else’s vacation at the dinner table every night.  Since we had so much alone time in the stateroom to be nude, I never pushed any clothing limits, and, with the crisp but not cold early summer Alaskan temperatures, wearing ski outfits or just comfortable and sweaters was fine.  We chartered a float plane in Ketchikan to show us the scenery from the sky.  We gave the pilot a few hundred extra dollars, so he wouldn’t mind when we took off our seatbelts and I got on my knees, undid Burt’s trousers, slipped them to his knees, cupped his balls, and teased his cock for about 15 minutes of “Oh God, oh fuck Dolly, oh shit, God yes don’t stop” until I let him finish in my mouth.  We landed on a private lake, and our pilot mostly watched out for bears while Burt and I laid down a blanket in a field below snow capped peaks.  After he went down on me, he made me his Alaskan lover for sure by pounding me as long as he could, given that he’d just cum less than an hour earlier in the plane, right there in the national park.  After the flight, I kissed the pilot on the cheek and squeezed his cock.  I sure hope that man got laid that night, because we made him so hard.

And then our post-coital stroll down Creek Street, a charmingly restored former red light district.  (It seems the hobby was legal in Alaska, or at least Ketchikan, until 1954.  I guess that was part of the deal to get statehood in '59.  What the hell, Utah gave up polygamy to get statehood.  At least, officially they did.  Wink.)  As it turns out, the most famous house on the street, now a museum, is called "Dolly's House.”  True story, friends!  You can Google it.

Ah yes, Glacier Bay, so much natural beauty, the majesty of nature.  Harbor seals sat on the ice floes with newborn pups, the glacier right behind them, while I did a reverse CG on Burt as we looked out through the glass door to the balcony. That was the balcony where I’d blown him during the beautiful sunset at 10:30 p.m. the night before, the breeze from the moving ship making it all so exciting.

This cruise ship also had a couples suite in the spa for side-by-side massages, with rose petals, champagne, and an hour of private time with a hot tub and a view of the ocean.  That was a much better way to spend a day at sea than playing Bingo.

We ended up extending the trip, as we wanted an extra day to unwind back in Vancouver at the end of the cruise.  So we called from Juneau (great crab legs at Tracy’s Crab Shack, BTW), and the airline and the Four Seasons were happy to make the changes.  The airline, of course, charged a fee that Burt happily paid, and the Four Seasons had only a luxurious top-of-the-line suite available on such short notice.  I wish I had time to tell you about that night in Vancouver, when we took advantage of the fact that so many television shows and movies film in Vancouver that I’d decided I was going to bring another gorgeous third party back to our suite as a treat for Burt.  He told me that he loved the idea, but I’d fucked him out the previous nine days, and he knew that not even Dolly with an industrial crane could get him up.  So, when he graciously said, “But it would be really hot to get to watch you with some hot stud type a lot younger than me,” I knew it would be a night to remember.  I called our girl from Blue Water, asked if she knew anyone who’d be interested, and, yep, Dolly, sexy Miss Vancouver, and that supporting role handsome stud puppet of an actor gave Burt quite the visual that night.



Purely fictional fantasy for your reading pleasure!

< Return to my blog