Going Anywhere For Lunch With Dolly
I swear, I was just trying to discuss why our firm should be hired to design the re-imagining and redesign of the man's yacht. That was all I had in mind when I suggested we meet for lunch.
Stop saying "bullshit", really, I didn't think of him sexually. At the time I suggested lunch, anyway.
So why did all that change when I read his reply email?
Perfect. We can work out a place later. I am game to come downtown and go anywhere.
Yes, I read that email, and all I saw was, "Let's fuck."
Must be in my programming. The default setting.
I'd been starting to do Dolly dates here and there, still keeping my day jobs and public commitments. All of which I still do.
But Chris --that was my "Go Anywhere" man, was probably the first time I became aware that my hunger for sex was no longer just a hobby, just an extension of a typical role for sex in a mature, consenting unmarried adult's life.
That's when I realized I saw sex, the potential for sex, the desire in others for sex, everywhere I looked.
Immediately I began thinking of lunch places. Located either in hotels, or next to hotels.
Then next, should I already have a room booked, and check in before the lunch meeting?
Too forward? Was I supposed to wait until I'd clinched the deal (the fuck, not the yacht) and then get a room? I mean, let him get the room. Oh hell, I didn't care at that point.
Maybe I should be adding more protein to my breakfast. Fiber, healthy plant-based carbs, all that, check, but maybe I'd been light on protein so my body was craving a man's "seed", with only my insistence on condoms preventing my body from being fed. Well, except for oral, when I always swallow so then literally I'd be feeding my body.
What to wear?
And then I wondered, "how do I reconcile my private life sex with Dolly dates?"
I quickly answered the last question first: Dolly dates are my business. Men who become aware of the potential for a Dolly date initiate the process. That expression of interest classifies that potential as a Dolly date, and they understand that its business. When I see a man and want him carnally, well, that's the non-hobby, civilian Dolly, me, on my time, feeding my hunger. My lust. Which I guess is still the core of how my life's different aspects co-exist so marvelously to this day.
"Go anywhere", he'd written.
Perhaps a catered lunch in a luxurious "love nest" type suite? If it was overlooking a marina, that would almost seem business-relevant.
I went with blood red for my manicure and pedicure, and went with black -- a form fitting dress that hugged my body, with enough of a scoop to the neck to accentuate the beginning of my cleavage. My hair was up, and the LBD was just long enough that you had to be really close in to see the tops of the thigh highs when I crossed my long, lean, toned legs. My lips, full and lustrous in a hue to match my nails. A mini-jacket that made the outfit look like "sexy business woman" instead of "sexy woman overtly planning to fuck the shit out of this guy she's lunching with". Like I said, "look like." Looks can be deceiving. I most certainly did want to fuck the shit out of him.
Well, almost. What I REALLY craved would be for HIM to fuck the shit out of ME!!
I was in my twenties. Chris? He was nearly sixty, married, wealthy, well known. He was older than my father. I didn't let daddy see me dressed to kill before I went to my lunch date, er, appointment. It was business, right? So, an appointment.
Nowhere had I stopped to consider whether he'd rethink the yacht contract, which would not only be a nice piece of business itself but which would also undoubtedly result in several referrals, if he slept with me. Maybe I was still in the "it’s like getting to play grown up when I fuck someone older than me" phase.
Sigh. I did love that phase. "Grown up." That phrase makes me think back to my high school friend, Mary St. Paul's father, Donald, when I claimed I couldn't find my keys and could he drive me home from Mary's week after graduation sleepover after everyone else had left including Lois St. Paul, Mary's mother, Donald's wife, who was a strict parent with Junior League attractive-type looks. Mary told me she had heard them arguing sometimes that Lois wouldn't do what Donald wanted to do in bed. Lois was Donald's second wife. His first wife divorced him when he fucked his company's summer intern, a college student named....Lois. Uh huh. One and the same. So Lois was no better than me. Except I really didn't want to buy the horse, I just wanted to ride it. Like a big girl. And I already knew I loved doing some of the things that Lois thought were strictly in the past now that she was nearly nineteen years into their marriage. Yes, do the math, Donald knocked up Lois, and lo and behold, divorced his wife and married her and made a new family. So we can assume sometime in the past Lois could suck a cock pretty well if he gave all that up. Still had a nice figure. Dressed way too conservatively for me to daydream about seducing her once I'd been initiated into the "Once-in-a-while-a-MILF-is-a- fun-lover-for-a-tight-sexy-barely-legal-teen Club". Okay, I did once touch myself one time thinking about Lois after a pool party. But apparently now it was all "lookie-no-touchy" or at least nothing other than vanilla. I was going to offer Donald way more flavors than Lois was serving.
I slid my hand onto his thigh, good old Mr. Donald St. Paul, and he had a chubby and didn't do anything about my hand. So I rubbed his cock, which was so inviting, through his slacks.
"How old are you Dolly?" he asked me.
"Eighteen", I told him, "so I'm legal, and I've dated older guys so I know how to please a man. There's a pullover up ahead if you want to, Mr. St. Paul."
Cock throb. Love feeling those.
I was young and on the pill and it was irresponsible to take his word for it that he was: a) clean, and b) vasectomized. I just loved the idea of my classmate's dad, an older dad for whom Mary was a "second family", was responding well to me. So I did him, without protection, one of the last times I've been so wanton and wild and careless.
He didn't last long, not that I minded, considering how hot it was to fuck Mary's dad. When he told me that he'd cum so quickly because I was so hot, I preferred to believe that it really was because I was so hot, not that he was a minute-man. But later, when we got together twice more that excuse started to wear thin. Donald was not one who could hold back. Whatever, it was so erotic, fucking my friend's daddy, having him cum inside me that first time, and then the next two time I'd pretend he was knocking me up, and imagine having his baby and then he'd leave Lois and I'd marry him and I'd be Mary's step mother. I'd imagine that as I oozed out of him, he reached down, and scoop up his cum on his fingers then feed me his finger and I suck it clean, tasting both of our sex juices frothed up together. But really, after that first time, we were screwing safe, using condoms. I never got any in me, I think he got scared after that first time, remembering back to Louis, but after he came those other two times I'd take his condom off, sucked him clean, licked all around. I was so psyched, fucking a grown up. A real, serious grown up.
Ah, youth, I was so much younger then. I swear, Donald might have soiled himself when I told him that I loved being with him and wanted to be able to go more places with him. Even grown-ups can get scared. It got the desired effect. Donald let me down gently, told me I needed to meet boys my own age and that our secret would always be special. He called the two thousand dollars in hundred dollar bills a gift for college spending, but I knew it was hush money. Some of the first money I ever earned in a sexual way. First thing I bought was sexy lingerie!
I don't tell my gentleman friends such things about wanting more from them, not anymore, not now that I'm a grown up.
So, being a grown up, I made up my mind to have a love nest nearby, have it fully stocked with everything a tryst might require, short of a defibrillator, and I ordered a glass of merlot which I thought was sufficiently grown up. I pushed a salad around my plate and ate none of it. All of my system was cleaned out and prepped for whatever might follow. Capiche? Yup, if the date was going to go to not just sex but anal sex, that was on the menu. Little did I know I'd never get there. Read on, there's more, don't worry....
We met, he was in a suit but no tie. We talked about local headlines, some recent political sound bites, and then the subject of the yacht came up. I asked him to describe the type of entertaining he'd like to do on the yacht and we would incorporate that into fundamental design.
And yes, by "what type of entertaining" I did mean, "will you be fucking hot women on this yacht about whom you'd prefer your wife doesn't know? Perhaps I can be your trial run...say, like right now?"
Problem was, by the time we got into this part of the discussion the bottle of wine I'd mischievously ordered when the plates were removed was mostly empty. So while I wasn't drunk or out of control, I did lack the discretion to make sure that the "fucking women on this yacht" line I mentioned above remained unsaid, in my mind only. Oh yes. Uh-huh. I said it out loud.
His eyes grew wide.
My nipples grew hard. Okay, harder. And I moistened out of hopefulness.
The silence made my heart pound. And then he said it: 'check please'.
In the town car to the yacht (it was close as the crow flies, but with the way the streets ran, it was a ten minute ride) I made out with Chris like a tramp on prom night, pulling his hand to my breast and grabbing his package through his trousers. Nice package. Nothing newsworthy, but they don't need to be, they just need to be healthy and willing.
Oh he was willing.
We went to the top deck, to the bridge. "Best views" was all he said. Well, that and "please keep your heels on, you've got amazing legs and they look great in those shoes, I love them."
He loved my legs, or my shoes? In my slightly alcohol-compromised state, I was having a moment of pronoun trouble. Which "them" did he mean when he said, "I love them"?
I giggled. Like it mattered.
He pressed me forward, "the better for you to see out" and then slid the bottom of my form-fitting dress up over my bottom. His hand found my increasing wetness. I was really fully ready and receptive by the time we reached the dock. He kissed the back of my neck, my shoulder, his hands on my now-bare hips and firm, toned ass. I parted my legs wider. He held himself close and I felt his cock, still in clothes (Damn! Strip, Mister, Strip!). But the fact that height wise, his cock was perfectly lined up to enter me made me glad he'd insisted I keep the heels on.
As I reached back behind me to grab a handful of his manhood, his lips on my neck found ground zero for that form of sensuous body kissing pleasure and my eyes closed, my head was thrown back, and I groaned involuntarily.
"Mmmmm, yesssss..... fuck me, please....."
He broke his kiss long enough to simply reply, "love to". And then I was aware of his hands removing his trousers and what proved to be a pair of boxer briefs with a serious pre-cum wet spot. Must have kicked off the loafers. Undid his shirt but kept it on. Kind of a dirty porn look, I imagined, since I was keeping my eyes closed to focus on the rest of the sensual stimulation.
Suddenly his arms wrapped around my waist and our bodies were tight against each other. His teeth nipped at my ear and before I could say anything he hissed, "Dolly, don't move or anything, I just need a second to get protection."
Oh, what a finely mannered lover he was. I was going to drain him dry, swallow his seed, talk dirty, open all of myself to him. Business? There was a business angle to this lunch? Not at that moment. I couldn't remember one.
Briefly wondered what the hell wine label it had been, the affect it was having on me, perhaps it was the best wine of my life, but this afternoon was soooooo definitely falling into place.
He slid his now-sheathed cock head up and down my wet opening. Teasing me. Back and forth across my clit, then back to the door to my core. The head parted my labia. And he stopped.
"No, don't stop, keep going...."
My God, that was ME saying that! Damn, usually I had the men under my spell.
I was totally his.
"Ask me, Dolly. Ask me what you have wanted to ask me all day. Ever since we planned this lunch."
Okay, I've got a body built for sex, a soul devoted to pleasure.....
And a brain that always, even in the middle of an orgasm, is always operating. I knew the wine was starting to wear through when the fleeting thought, "well, when I planned the lunch originally I wanted the contract to renovate your yacht. You want me to ask you for the sale now, here, like this?"
Okay, sarcasm. Instead, I let that wise-crack keep going and it passed out of my consciousness, and instead I asked him the question he was much happier to hear, "Will you fuck me, Chris, please, fuck me, I need your cock inside me, will you?"
I felt his cock pulse and it sunk maybe an inch further. Or is it "farther"? Do you guys mind imprecise grammar brought on my erotic, taboo, illicit, raw sex?
Yeah, fuck that. Anyway, he pulsed, he liked the pleading. I gave him more of what he wanted, knowing I would get more of what I wanted.
Another cock-pulse. Reminded me of Donald, the way he pulsed that first time. I never tire of feeling a man's cock pulse with excitement when he knows he's going to get to fuck me.
"Can I be your hot fuck girl Chris? I'll do anything you want, you can fuck my mouth, fuck my ass, cum on my tits, I'll lick your cock clean after you cum, oh God, you can fuck my face and cum in my mouth, oh God, please, I need you to make me yours."
Another Donald memory. Stuff Lois wouldn't do was included on that list.
Chris' nice cock hammered my pussy with his hands on my hips, my arms bracing myself against the control panel. Maybe a minute in, he backed away.
"Shit you're gonna make me cum too fast you're so fucking hot Dolly."
Good, this time the older man fantasy fuck was going to last a bit longer.
He interlocked his fingers with mine from behind and he moved backward into the very Captain Kirk-like captain's chair on the bridge. I was able, with a bit of contortion, to turn and mount him, facing him, cowgirl style, still in my heels, and ride his cock up and down, his hand on my tits, my hands on his chest, my eyes on his, and occasional kisses. I felt his hand go to my shoulder and pull me down hard as he thrust up with more power. His balls were getting ready to erupt in me. I scrunched down on his dick with my inner core muscles. What a sense of power that gives me, by the way, squeezing you wonderful men like that.
I raised myself up and off his ready-to-fire missile, reached down and squeezed that cock at the base.
"Let me help you last, Chris, I want you to enjoy me as long as possible, keep fucking me."
He pulsed in my hand when I said that last part.
I looked in his eyes. "Do you want me?"
'No, Chris, I asked you, Do ...You ... Want ... To ... Fuck ... Me." My turn to ask now.
"Yes, Dolly, I want to fuck you."
"Will you fuck me hard?"
"Say it all, Chris."
I bit his nipple, hard enough to arouse him, not enough to hurt him. Not too much, anyway. I was hovering above his cock, thankful for strong legs when I was in an awkward crouch, teasing my clit with his still-condom-covered cock.
"I want to fuck you hard, Dolly. Please, please let me fuck your sweet tight pussy hard with my married cock, I want you full of my cock, feeling me inside you, please Dolly."
I bit my lip, looked in his eyes, and kissed him, this time with passion rather than hunger. Softer, more sensually. And I lowered myself onto him, leaving my hand between us to twiddle myself.
"Then fuck me, Chris, fuck me till you cum, but let me know when you're about to." And then my mouth returned to his.
He did as he was told.
He remembered the contract and took it from my oversized purse to sign it not long after, while I was wiping his seed off my tits and licking my fingers clean. After I licked each finger clean, I placed it in his mouth. He sucked my fingers, playing with them with his tongue. I wanted to feel that tongue on me. Downstairs.
And the contract was signed.
As far as I'm concerned. The rest of the afternoon was unrelated to the deal, the contract was already signed. The evening, too, after he'd licked me to a pair of really satisfying climaxes, when I gave him my back entrance and felt him pulse and spurt in the condom and stiffen and climax while buried up there, that was also after the contract was signed.
And the weekly sessions during the ship re-design phase, to act out the rest of his sex fantasies, those were just the two of us being consenting adults, too. I told him I wanted him to sample all his fantasies.
Though since one fantasy involved sisters and I could only oblige him with a former sorority sister who was taking a year off from her modeling career because the travel was getting to be too much and she was instead earning really great tips as, of all things, the sexiest house mom in a strip club you've ever seen, we didn't fully live that one out. My sister is hot, but I wasn't bringing her into my tawdry affair with Chris. I know what you're wondering, have I ever done anything with her, other times? Keep wondering, boys.
So instead of my real sister, it was me and Peggy (her real name). Peggy was a natural to serve as a stand-in sister as she and I had done some three-ways in college, and once at a wedding and once at a reunion. Interestingly, all those three ways were with the same guy, ironically he became the husband of another of our sorority sisters who was a sweet girl with family money who was, sadly, a lousy lay and we all knew it. Their marriage didn't ultimately last, but if anything, the couple of thrills Peggy and I had with him kept them together longer since we'd say after each on, "So glad your sweet Janice just can't keep up with us sorority sister sluts, we get to enjoy you so much!" Yes, including the morning after their wedding! Ah, the joys of fucking Janice's boyfriend, later fiancé, and then finally her husband with Peggy, and now I was pretending Peggy was my sister. Mmmm, that girl tasted so aroused and sweet and creamy, no way she was just faking when it was girl on girl time. Yes, sigh, Chris actually thought Peggy was my sister so he didn't know we weren't really acting out his fantasy. Did it matter, the sex was hot! Or if he figured it out he never let on. Having her snowball me with a mouthful of his seed, followed by some seriously cum-flavored girl on girl making out and a sweet, "thanks, sis, fuck I've missed you!" seemed to turn him on either way.
Chris invited me, my naval architect, and the head of our company who just happened to be my dear beloved Daddy, to the refurbished yacht's christening party. Big group on a big ship, probably about one hundred and fifty or more. Chris' wife was there, a stern look on her face when she met me. Did she know? Probably. Women know. We have a sense for such things. She rolled her eyes when Chris came by, saw us together and stammered out, "Oh, hon, this is Dolly, she's the yacht contractor's consultant. She was a big help, hon!"
"I'll bet you were," she said to me, and that clinched it. She knew. But she hadn't stabbed me with a shrimp fork or anything else that was sharp at the buffet. I was going to survive! She shook her head a bit side to side, a "tsk tsk" expression on her face, took his chin in one hand, her left hand, showing a flawless pearl manicure and some serious ice on her ring finger, and kissed him. "Be a good boy, Chris, okay?"
Oh, she knew.
My father rolled his eyes. Oops, after seeing the wife's reaction, Daddy knew too.
As we disembarked, he laughed to himself. "Dolly, oh....never mind, I love you dear, see you for brunch on Sunday."
And wouldn't you know, when I showed up for brunch with some terrific muffins, my dear mother had that, "We love you but why do you have to be such a bad girl, Dolly?” smirk on her face.
It’s just how I am.
Then Mom winked at me when I handed her the muffins. I smiled. Mom was so cool!
Ah, good times.
Gotta go now. Another lunch date. Business, strictly business. *Wink!
Purely fictional fantasy for your reading pleasure!