Dolly's New Years Eve
It was New Year’s Eve, just a couple years ago actually. I looked out the window of my 34th floor hotel suite overlooking Times Square. There was a massive crowd below and it was only 9 PM. And above it all … that ball. You know. THE ball. The one that’s been dropping for decades above Times Square with the crowd in the streets screaming, “10, 9, 8, 7, 6, 5, 4, 3, 2, 1” and then in big neon lights the words HAPPY NEW YEAR lighting up below it.
I watched it for years on TV as a kid, then for the first time as part of the crowd when I went to New York with my college girlfriends. It was SO cold that night and we got SO drunk, the memory of the ball that year was a blur. I honestly don’t even remember it dropping.
But this year was going to be different, VERY different. I’d rarely come to New York on New Year for “Dolly Dates” but I had a special friend in New York who begged me to spend New Year’s Eve with him. He was actually flying in that evening from overseas and wanted a “really special” celebration to kick off the New Year. I was more than happy to give it to him.
So let’s talk about “special”. To me that meant finding a terrific hotel suite with a view of the “dropping ball”, flying in early that day to do some shopping at my favorite NYC lingerie store, buying just the right bottle of champagne, and getting ready to blow his fucking socks off at midnight. At the stroke of twelve I had plans to have not one but two balls drop in a way that would make the Times Square experience totally minor league.
So there it was, 9 PM. I had just slipped out of a luxurious bubble bath and was preparing for a scorching hot New Year’s seduction. I pulled my new lingerie out of its box and began running my fingers over it … the black lace bra that left virtually nothing to the imagination ….the black thong G-string and panties that were so damn sexy I almost came putting them on … then of course the stockings and heels … thigh highs and stilettos … black of course. As I looked in the mirror putting on my lipstick, I could just imagine how his hard-as-a-rock-cock would look with that red lipstick ring around it. I LOVE that look on a cock … especially when I look right up at the guy with that pouty, “Oh … I’m sorry … do you want me to lick it off?”
I was already so wet and hot I had to lay in bed for a few minutes playing with my clit. I’ll admit it. When it comes to sex, I’m insatiable. There’s just no other word for it. I could come twenty times a day if given the opportunity (and actually have a few times.)
The object of my affection was due to arrive at the hotel at 10:30, and I had my plan all laid out. My goal was simple: to get him to cum EXACTLY at midnight. And I mean EXACTLY. When the ball dropped outside, his balls would drop inside after exploding a load … right into my mouth. It just HAD to be at midnight.
I figured that to make this work, I’d have to tease him slow and hard to make him last 90 minutes after he got there. So I brought along my killer black gown … the one that takes a dive off one shoulder and nearly ALL the way up one leg. There’s no way I could greet him at the door in my new lingerie or he’d be shot within minutes.
After he arrived, I’d pop the champagne and order some room service. He would probably be hungry having just flown in and there was no way I was going to have a guy lacking energy in this room for the show I’d prepared for the night.
Then I’d tease him like he’d never been teased before ….a slow seductive strip, followed by long, luscious deep French kisses that would make the French themselves blush. Then, of course, the bareback blow job. And not just ANY blow job. This would be a first class tease & denial version. Just a few light licks at the back of the head, then back off. Then a few more …. maybe adding a slow, long lick under the side. Then, I’d turn my mouth into a dripping wet pussy … but with ME in control … letting him fuck my mouth but being OH so careful not to let him go too far too fast … before midnight, that is.
That’s probably the biggest issue I face in my hobby. (Don’t you just love that term “hobby” … reminds me of collecting toy trains, dolls or coins. Actually I admit I’ve received quite a few “coins” in this hobby but not the collectible kind.) The issue I’m talking about is getting a guy totally aroused but NOT so much that he blows his load within five minutes of walking in the door. Believe me, it’s happened. Pretty frequently. And I certainly don’t mind, especially if he’s the type who can be ready for another round fairly quickly. But if a guy is a one-timer, I feel guilty for not being able to have him enjoy the “full treatment.”
Then my plan was to slowly but VERY sensually work him through every position we enjoyed, and when I knew we were about one minute away from THE ball dropping, I’d take him to the window so he could watch both the ball going down and me going down on his cock, so he could do his own countdown, climaxing with, well, A CLIMAX exactly at midnight … a hot load directly into my mouth. I’d then gently let his cum run past my lips into two glasses of champagne and we’d toast the New Year with I guess what could only be called a “Dolly Mimosa.” (Who the hell needs fresh orange juice when you have fresh cum to mix with your champagne!)
So it’s now ten o’clock. I’m expecting him in thirty minutes and I’m totally ready. I stand in front of the full length window looking down at the square wearing only my lingerie, wondering if anyone down there can look up and see me. I laugh to myself, “what if some guy and his girlfriend are standing in the square and he looks up to where I’m standing?” No, I decide, not a good idea. That would be too tough on his girlfriend.
But just when I start thinking about putting on a bit of a show at the window, the phone rings in the room. “Shit!”, I think. “Is he already here? Is he downstairs? I haven’t got my gown on yet.” I pick up the phone, and yes, it IS him, but he is NOT downstairs. In fact, he is calling from the first class phone in his airplane seat because the pilot had just announced they’re circling above LaGuardia due to bad weather and may need to land in Newark, or possibly worse, Washington Dulles!
UNBELIEVABLE! Here I am on New Year’s Eve, expecting one of the highlight nights of my hobby career and he’s not going to make it by midnight! In fact, if he goes to Dulles, he’ll be lucky to be here by tomorrow afternoon!
The gentleman that he is, he apologizes profusely, generously explains that regardless of his being able to make it, he’ll take care of my time and expenses.
But then … that’s it! (It was obvious he was talking on one of those plane phones between seats so he couldn’t be too specific, but I got the “message”.) He and I both hung up and I literally dropped into the bed thinking, “Well, this just may be the worst New Year’s Eve I’ve ever “celebrated” and I’m doing it alone.
I looked out the window again and for a brief moment thought maybe I should just go down with the crowd, get rip-roaring drunk and call it a night. But I just wasn’t in the mood. I turned on the TV to watch the festivities, popped my bottle of champagne and laid there, taking a drink. And now I was hungry, so I called room service and ordered some olives, cheese and chocolate cake. This was one night when I was going to need all the comfort food I could handle.
Twenty minutes later, there was a knock at the door. I grabbed my robe, put it on and the room service guy rolled the cart into my room. Honestly, I didn’t really even notice him as he passed me as I was holding the door open, but when I turned to watch him remove the covers from the dishes, I COULD NOT BELIEVE MY EYES! There was the most GORGEOUS, HOT, TANNED, YOUNG, MUSCULAR guy I had seen in a LONG time. (Okay, maybe I’m exaggerating a wee bit, but hey … I was hungry, lonely and horny. I would have ordered HIM if I’d see his picture on the menu!)
He very efficiently and quickly had my table ready and gave me the check to sign. I took it, thinking to myself, “How in the world can I keep this young guy – he couldn’t have been older than 25 – in this room until midnight and give HIM a night to remember all of his life! On the house, no less, because my client was paying all the bills!”
“So,” I said, allowing my robe to open just slightly to reveal cleavage he OBVIOUSLY noticed. “Someone actually has to work on New Year’s Eve? That’s a shame!”
“Only another ten minutes,” he said. “I’m off at 11:30. In fact, you’re probably my last stop for the night.”
OMG! I don’t think I ever previously felt my pussy go from dry to dripping wet in five seconds. Have you ever had a moment when you felt the stars were aligned JUST for you? That was how I felt. It was like I just won the lottery, and I literally jumped on his line, trying to be cool, calm and collected when I was really hot, excited and very UN collected. “I see, well that makes sense. I mean there probably aren’t many people ordering room service in their rooms on New Year’s Eve at this time either … I would imagine.”
“No,” he said, noticing my gown hanging nearby. “Are you on the way out to celebrate? That’s a very nice dress.”
“Actually, no”, I confessed. “To be perfectly frank, I was supposed to meet my boyfriend here and he just called to say his plane is delayed and he won’t be making it tonight at all. So I’m here … all by myself … alone …”
Now I have to admit, I’ve got some practice behind me in the art of seduction, so I really do know a lot of the right moves. After that last line, right after “alone”, I untied my robe belt and dropped it to the floor. Call it what you will, a “Mrs. Robinson” move from THE GRADUATE or whatever, it definitely had the desired effect. I thought this guy was going to keel over. As he stared at my humbly described drop-dead body in lingerie that would even be too sexy for mares on a stud farm, I asked him, “would you like to see me in the gown?”
I’m sorry but what happened next is just downright funny. This poor kid was literally shaking like a newcomer to the porn industry in a MILF film. I laughed and asked, “If you like, I could put the gown on for you ….or ….not.” And with that last line, I reached behind, undid my bra snaps and dropped it to the floor. Tommy’s eyes popped and he literally began to sweat. I was having SO MUCH FUCKING FUN, I honestly wish I could have captured this on film FOR one of those MILF movies.
“What’s your name?” I asked. “T..t…tommy” he mumbled, his eyes glued to my tits.
“And do you work here part time, full time?”
“Part time. I’m a graduate student … at NYU … majoring in … biology.”
I laughed again. “Tommy,” I said. “I have a proposition for you. If you just stay in my room with me another thirty minutes, until just after midnight, I guarantee you will have a biological experience you will remember the rest of your life. Will you do that?”
“Well … uh … since I’m ending my shift anyway, I guess …. I guess so … but …”
“But what Tommy?” I asked as I moved closer to him, brushing my tits against his side, reaching down to barely graze my hand over the bulge in his pants and whispering into his ear, “Is this … hard … for you?”
OMG #2. I’ve seen a fair number of cocks leap to attention in my presence, but Tommy’s just about tore a hole in his trousers. I laughed again. Tommy had no idea he had essentially walked onto the stage of a theatre just as the curtain was about to go up and he was about to become the male lead.
“Tommy, I just want you to lie down on the bed, take off all your clothes, and watch me for a few minutes, okay?”
Tommy’s answer “okay” suddenly had a different tone about it. I had crossed the Rubicon. Fear and trembling was beginning to change to “Am I living a wet dream?” Tommy stripped so fast his clothes flew across the room, and I began what might be the best strip tease of my life. I looked at the clock, saw a half-hour to kill, and there was NO WAY I was going to let this kid cum before the stroke of midnight.
Since my bra was already off, I took some coconut oil (I always have it with me, love the stuff), poured a bit on my nipples and let it drip down my body, my hands rubbing it in. Tommy’s cock was already so fully erect, I was actually concerned he was going to cum without even being touched. “Now take it easy, Tommy,” I said. “Just relax, and keep your hands by your sides. I’ll handle all the touching, okay?”
He nodded and I continued … placing a black-stocking-covered leg with a stiletto heel on the bed in a classic “Mrs. Robinson” position. I took off the shoe, then slowly rolled the stocking down. I thought Tommy was literally going to die.
“Why don’t you take a drink of champagne,” I said. “Something to cool you off.” I poured him a glass. But his hands were shaking so much he could barely hold it. So I held it for him as he sipped, with my other hand gently massing that now MASSIVE, and I do mean MASSIVE cock. Then my lips touched his. And I gently but firmly thrust my tongue into his mouth like a knife cutting the first piece out of a cheesecake. Tommy was SOME kisser. Phew.
Within thirty seconds we were lying side by side in bed, our tongues dancing a tango in our mouths, my legs (especially the one still wearing a stocking and stiletto) sliding against his cock. I really was concerned that Tommy could cum any second but I decided to risk it and pulled a move I simply LOVE. I raised the leg with the stocking and heel and wedged his cock right between the base of the shoe and the heel, rubbing it up and down … a move that ALWAYS drives guys crazy, whether they’re into foot fetishes or not. And it definitely had the planned effect on Tommy.
I quickly stopped and pulled away, looking at the clock. It was now 11:50. “Just ten minutes to go,” I thought. “If I can just make him last. I need a distraction.”
It looked over at the untouched room service table and immediately seized on the moment. “Tommy,” I asked. “Do you like chocolate cake?” Again, he nodded, barely able to speak. I reached over and moved the plate over to the bed. But I did NOT take a fork and give him a bite. I ran my hands through the icing and then ran them right across and into my pussy. “Would you like a taste?” I asked.
Have you ever seen a puppy that hasn’t eaten in weeks dive into a bowl of food the second you put it in front of him and watch him lick the bowl clean? Yep. THAT was Tommy. Damn he loved that cake, I mean pussy, I mean cake AND pussy, I mean ….you get it. And the more he licked that “bowl” clean, the more I FUCKING LOVED IT! I mean seriously, if I’d known chocolate cake could be used in this manner I’d have bought a Betty Crocker cookbook YEARS ago.
My pussy was so on fire I WANTED Tommy inside me so bad that it HURT to see I still had five minutes to go. But I’ll be totally honest, I JUST COULDN’T FUCKING WAIT! I reached over to my handbag, grabbed a condom out of my bag, slipped it onto Tommy’s cock and said, “I think you’d better dig a bit further. You missed some frosting.”
HOLY SHIT!!!!! Tommy now grabbed his OWN handful of cake, “lubed up” my pussy again with it, and literally DOVE in with a cock that was now harder than the best dildo I’d ever used. Where was this kid when I was 25?
Tommy really knew what he was doing too. He started out slow … letting the frosting get moister and moister (Betty Crocker would have been proud) … then it was time to turn on the electric mixer! DAMN! He pounded away and I literally screamed in orgasm as I looked at the clock and saw it was 11:59!
Tommy must have thought I was nuts, but damn it, I had a plan! Literally in the middle of a mind-blowing orgasm, I threw him off me and told him to go to the window, “Tommy, the ball is going to drop!” I could tell by looking at his face that he was totally bewildered but he went along with it.
And there, at the window overlooking Times Square, I saw the ball just starting its downward last-minute slide. And I tore off Tommy’s condom to start my own “slide” with his cock into my mouth. I could tell he was ready to explode any second but I viewed this like I viewed my strategy the last hundred yards of a triathlon. “Pace yourself,” I thought. I licked him until 30 seconds, took him all in at 20 seconds, and as I heard the crowd below chanting, “10, 9, 8 …” I rammed his cock in and out of my mouth like a piston on a Porsche. When I heard “4,3,2,1 …” I deep-throated him so fast and hard I could literally feel what seemed like a pint of cum flying into my mouth!
“YES!!!!!!! MISSION ACCOMPLISHED!!!!!” Tommy was so exhausted he literally fell to his knees while I grabbed our two glasses of champagne and watched his eyes in disbelief as I let that cum drip from my mouth into those glasses and gave him one to share a toast. Even Tommy was now blown away (literally I might add.) I just looked into his eyes and said “Happy New Year, Tommy.”
“Damn! Are you for real?” he asked. “How often do you stay at this hotel? I may get the hell out of grad school if I can get this kind of treatment doing room service!”
I howled. “Tommy,” I said. “This is a once-in-a-lifetime experience. We were both at the right place at the perfectly right time. Don’t quite your studies. Just consider this a biology (and psychology) lesson worth a LOT of extra credit. And I officially give you an A+.”
I could tell that Tommy was about ready to sleep for four days after this thirty-minute New Year’s marathon, so I helped him get dressed and out the door. He was gone by 12:15
Then I went back to the window overlooking Times Square. The crowds were starting to break up, the “big event” was over, and a new year had begun. For me, what was going to be a major disappointment turned into one of the most memorable experiences of my life.
So on behalf of Dolly Jewel, Tommy and the room-service workers of America, I would like to thank the City of New York for letting their “ball drop” yet once again that New Year’s Eve. It will be one I will NEVER forget.
Purely fictional fantasy for your reading pleasure!