Fabulous Weekend

by maryjane

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Oral Sex, Anal Sex, Squirting, Water Sports, .

Desc: Sex Story: Dan and Trudy meet in a hotel bar, each intent on raw sex. The lust turns to love. This one is told from both his and her viewpoints.


Below the waist, I'm all woman, plus a little bit of Greek boy. Above the waist, I'm like a boy. All of which means that I can't push my tits up or out, or flash them a little, in order to attract a guy. Fortunately, I get by without using them. Shaking my ass when I walk does the job easily. Five foot one, one hundred five pounds, green eyes; they tell me my eyes twinkle. My hair is blond, both head and pussy, but my mind is not. I keep my hair in pigtails, like a German milkmaid. I'm twenty three, a well paid paralegal.

It was five thirty on a Friday evening. I was sitting at the bar in the Four Seasons, around the corner from the office, wondering what the evening would bring. I could feel my boss' cum leaking out of my cunt, soaking my panties. Like a typical lawyer, he fucked the women in the office and then went home to his wife and kiddies, so weekends were out. Actually, he was nothing but a pretty good cock; I didn't know if I was well paid because of my brain or my cunt, and I didn't care. I would not have paid him to be my lawyer, but his cock was just fine. Only that afternoon he had been in such a hurry to go home to wifey that I never got to cum. I had decided to leave the wet panties on to see if my scent sped up the evening. Of course, I had two pair of dry panties in my purse. Ever the optimist, I always expected to need dry panties when I went to a bar.

"Can I buy you a drink?"

"Yes, thank you. I'd like a tablespoon or two of your cum shooting into me, swirling around in my mouth, but I'm saving my virgin mouth and cunt for my future husband."

"Don't be like that, Trudy. I told you I'm going to leave her."

"Bullshit, you've been saying that for too long. I'd rather be in a nunnery. Get the fuck out of here."

Another lawyer. I wondered what excuse he could use to come home late on a Friday night.

"Excuse me, ma'am, is anyone sitting here?"

I had seen him in the mirror, walking toward me. Lean, handsome, ruggedly so, he made my pussy twitch just looking at him.

"Actually, I've been saving that seat for you."


I was sick and tired of this place, I mean, it's a great tourist city, and the company pays for a fabulous hotel, but still, four weeks of living out of a suitcase is too much, and I had two more weeks to go. Meetings, negotiations, contracts, due diligence crap, my brain was frazzled. Add to that the fact that my girl friend was three time zones east of us and quite likely by this hour back there had some guy's cock in her ass already. She was a great piece of ass, and I didn't mind sharing, but I think she was too much of a slut.

My problem is that I like to fuck, have never had much trouble getting it, and was stuck here in a city full of strangers. The people I was dealing with invited me to some home dinners, but there was never any action there. All the weeknights were too busy for any prowling. I've never had to pay for it in my life, and I had no intention of calling up some "exotic dancer" from the Yellow Pages. As a result, I had to get myself off most of the time. The upside was that I get a kick out of sleeping on a wet spot; call me weird.

Weekends were ok. Too many of the women in the hotel bar were hookers, but I could usually spot the amateurs. Last weekend was a problem, though. I was straddling this broad's chest, pumping away, when she took my cock out of her mouth, jerked my cum onto her tits, and asked me how I would like to be doing that every night for the rest of my life. Well, I thought, definitely yes, but not with her. I couldn't very well say that, so I just smiled. The problem was that she knew my room number, even though I hadn't given her my last name, so after two nights of her calls, I had the hotel change my room.

The day had been a bitch. Negotiations about one of the subsidiaries was threatening to break down over some fishy stuff on the books, and there was a lot of screaming going both ways. Finally, at five o'clock, I wrapped it up. "I want to see details of every item over five million by first thing Monday morning. Tell your families that they won't see you until Monday night, unless I'm not satisfied, in which case they'll see you Monday before lunch and I'll be on a plane back home at noon."

As a result, I was still ripping mad when I walked into the bar. Nobody fucks with Dan Cassidy. I needed a drink, badly; I had no interest in scouting the delicacies sitting at the bar. I stood by the door, letting my eyes adjust to the darkness in the room. The sound from the couple at the bar was whispered but she was obviously angry. I heard her spit the word "bullshit" out of her mouth, and after a few other words I couldn't make out, the guy left.

Her anger and language did not to me seem to be the reactions of a pro arguing price, but of a young woman angry at the conduct or words of a man she knew, biblically and often. I decided that I need not drink alone, and maybe I could wrangle dinner and a fuck without looking any farther. Though she acted like a grown woman, the pigtails took years off her looks. She saw me in the mirror as I approached, and did not turn her eyes away.

"Excuse me, ma'am, is anyone sitting here?"

"Actually, I've been saving that seat for you."

Well, well, well.


"Why, thank you. I couldn't help noticing you having a few apparently well-chosen words with the gentleman who just left, and I thought a drink would calm us both down, for I've been having a bad day also."

"Yes, thank you. I'd like a tablespoon or two of your cum swirling around in my mouth." Only this time I didn't say it out loud.

"I used to go out with that bastard, but he never told me he had a wife."

"Wife? What's a wife?" He smiled as he said it, flashing his ring-less hands. "Never had one, though I've heard of people who speak well of them. I'm Dan, by the way."

"Trudy, short for Trudy."

"Ah, that explains the pigtails. Very attractive."

Perceptive son of a bitch, this Dan. The bartender hovered over us. "I'll have some white wine, please."

As Dan said "Bourbon, straight up, please," I stole a glance at his crotch. It looked solidly packed; maybe I wouldn't have to spend too much time in this bar. Could he smell the cum in my cunt?

"What brings you here, Dan?"

"I'm from back east. My company buys and sell other companies, and my job is to make sure that what we're looking to buy is really legitimate. This hotel is fabulous, but enough is enough. I just finished week four out of six, but unless the people from the other outfit straighten out their act, I may be gone on Monday. You?"

"I work as a paralegal right around the corner. Lived here all my life, twenty one, also never been married." Don't look back, I did tell you I was twenty three, but he didn't have to know it.

We sipped our drinks, making lots of eye contact. The cum had finally all run out of my cunt, but it was wet from fresh juices, and I knew that later tonight it would be wet again from fresh cum.

"Could I trust you alone for ten minutes while I go upstairs to wash and change? I feel grungy from a tense day today."

"I don't think you can trust me. Why don't we take our drinks upstairs so that you can keep an eye on me and make sure I don't run away?"

"That's nice, but I would like you to stay for dinner, also."


I couldn't identify the specific scent, but I could tell that this woman was in heat. I wondered if she had been fucking someone in her office before she came to the hotel.

I made some remark about noticing her having a problem with the guy who had left. It turned out to be over the fact that he was married. Stupid fuck. Although I've never been married, I knew enough to know that he should have been wearing a ring, to let the broad know right off the bat that all he wanted was cunt, and that she shouldn't get any ideas. Once in the past, I had actually thought about buying a ring just for that purpose, but had dismissed it. After that girl the past weekend, maybe I should rethink it.

Her voice had a happy tone; she could have trained her voice to be sultry, but didn't have to. It would also have been nice if she could train her tits. She had tits like Twiggy-remember her-nothing but nipples pushing out. ("Wow, Twiggy, you have no tits." "Get off my back.") She obviously didn't need a bra.

She ordered a mild glass of wine; maybe she was in the habit of wanting to stay clear headed for the sexual chase. I ordered something stiffer; I was pretty sure that we would be out of the bar after one drink. I wasn't then certain if I would be having steak or pussy for dinner, but it wouldn't take long to find out. I decided to go for the jugular. It was even partly true.

"Could I trust you alone for ten minutes while I go upstairs to wash and change? I feel grungy from a tense day today."

Damned if it didn't work, although I never really doubted it. I wasn't going to need a brush to wash my back that evening. My cock was pressing against my zipper as I signed the check.


"That's nice, but I would like you to stay for dinner, also."

Mr. Dan didn't have to worry about that. I had already decided that a mouthful of his cock was to be my appetizer. He picked up both drinks and stepped back to allow me to walk first toward the elevators. It wasn't the first time I had used those elevators, but that's a story for another time. I could feel his eyes caressing my ass as I walked. I pushed a button and the doors slid open, noiselessly.

"Twenty three, please." His hands were busy holding the drinks.

"Ah, my age."

"I thought you said twenty one."

"Oops, you caught me." I laughed as I said it, but I felt like shit. "Shall we go back down and wait two years?"

"I hope that you not having a husband isn't also an oops."

"The rest is all true."


We walked quietly down the hall toward his room.

"My hands are busy holding these drinks. I can't get to my key. Would you get it please? It's in my left hand pants pocket."

I couldn't resist. I moved behind him, put my left hand into his left pocket and wrapped my right hand around him to rub his cock through his pants. My left hand felt the key, but went past it to rub his cock from the other side, through the pocket. He squirmed.

"Do you want me to spill these drinks?"

"I don't care." But I stopped playing, took out the key card and led us into the room. I noted with delight the fact that he had a king size bed. He put the drinks down and turned. I reached up to put my arms around him and bent him down for a kiss. I was pleasantly surprised when he kept his tongue in his mouth, not trying to immediately force it into mine. It seemed like it took forever for my hands to undo his tie, his arms having taken over the job of holding our bodies against each other. Still connected at the lips, we went to work on each other's shirt buttons. He finished first and slid a hand in to tweak my nipples.

With very little meat on my tits, my nipples were always the point of first contact, and they relished the job, having been at attention for the last twenty minutes. As I started on his belt, he reached behind me to the button on my skirt. Suddenly, I remembered that my panties were all wet and I stepped back.

"I'll do those," and had skirt and panties off and on the floor in an instant. He didn't seem to mind; his hands gripped my ass. I pushed him onto the bed so that I could get his shoes and socks off, then his pants and shorts. I love it when I take down a guy's shorts and his cock pops out in my face.

"Get off the bed and help me take off this cover."


All this due diligence work I do has trained me; I'm always on the job.

I noted without surprise that she knew her way to the elevators. I assumed it was not her first unregistered stay in the hotel but I didn't mind. I certainly did not want to break a virgin cherry that night.

It was a surprise to catch her lie about her age. It seemed to me that it was not important to lie about; one should lie about important stuff. It's very difficult to remember a lie, so why strain your brain on trivial lies?

Carrying both drinks was a ploy I've used often. Give her a chance to get her hand in my pocket and see what happens. By the time we get to that point, there's no doubt that I'd be fucking her, but it's an interesting way to begin the ritual.

I don't think I was supposed to notice that she took off her own panties, while for everything else, we undressed each other. Later I'll check to see if the panties are too wet for it to be her own lubrication.

For reasons I can't explain, since I am fond of tits, her flat chest really turned me on. Maybe I'm an unknown latent pedophile. The nipples, however, made it clear that she was a mature woman.

So did her cunt hair; her twat matched her head in color, it was silky and not too thick. I ran my fingers through it while she took off my shorts, but she was so focused on my cock that I don't think she noticed my fingers combing and stroking her.


Enough of this foreplay; I wanted cock in my mouth. With the covers off, I pushed him onto his back and knelt between his legs. I held his dick pointing toward the twenty fourth floor, my mouth straining to get both his balls in at the same time. I sort of gnawed on them while also licking as well as jerking him off. After a minute or so, I released his balls from my mouth and began to lick the underside of his cock before taking him in as deeply as possible. He sighed.

"How much is three times your age?"

"Sixty three."

"Your real age, silly."

"Oh." With that, I walked sideways on my knees, in a circle, until my pussy was directly over his face. I squatted down so that his tongue could reach my lower lips. His firm hands spread my legs from below as his mouth devoured my pussy, moving to suck my clit like a baby while sliding a middle finger into my ass. Surprise, Dan, I'm a squirter when I cum. My juices poured onto his face; he opened his mouth to receive as much as possible, drinking it in without hesitation, the rest spilling onto the sheets.

With my own orgasm out of the way, I attacked his cock with a vengeance, my head moving like Woody Woodpecker, my hand caressing his balls, finally to duplicate his action by searching for his prostate. The intrusion was the trigger, his cum zipping from his balls along his cock into my mouth. It tasted like a commercial: smooth, creamy, tangy, delicious.

"How long have we been in bed, Dan?"

"Ten minutes, tops."

"How long does it take you to get it up again?"

"Do you want dinner up here or in the Dining Room?"

I thought a moment. "Let's get dressed and go downstairs."

"It's a deal."

Still naked, I rolled over to the phone and dialed home. I get my looks from my mother, and expected that she was out catting around herself, but I was waiting for the four rings to start the answering machine. "Hi, mom. I won't be home for dinner. I probably won't be home until Monday morning in time to get ready for work. If you need me, call my cell phone. If it's not on and it's important, call the Four Seasons, room 2306."


I loved the feel of her mouth on my cock. It's great when the girl doesn't waste a lot of time, just latches on like it was a tit. Such a warm, moist mouth, great hand giving me a great hand job, devotion to my balls. I would break my own rule and pay this girl, willingly.

One thing I love to do is to talk in circles, like asking her the multiplication question instead of just telling her that I wanted to do a sixty nine. Funny how she either didn't figure out what I was asking for, forgot that I caught her lying about her age, or just wanted to psyche me out. When she came around, though, it was the best cunt I'd tasted in years. Whether it was the fishy scent, which turns me on, or the creamy taste of her pussy, which was too thick to be lubrication, maybe it really was the cum from some guy earlier today, I didn't know, didn't care, but I couldn't get enough of it.

Usually I try to keep them on the hook as long as possible before I let them cum, but I liked this one a lot; I wanted her to cum "early and often", like a Cook County voter. Also, her aroused clit stuck out like one of her nipples, and I couldn't let go of it until she came.

As the juice poured out of her cunt when she came, I thought of the first time I ever had that happen, back in college. I always enjoyed it, considered it a special treat, but didn't get it often enough. And the bonus was, whatever I didn't get in my mouth gave me a wet spot to sleep in later. Unless we fucked so much that it dried up by then. Of course, if I kept making her cum, she would keep the bed wet all night.

Like I said, I prefer women with experience, but the way she was moving her head on my cock had all the earmarks of a paid professional. She was better than good, she was exceptional. I tried to keep the finger in her ass moving in time with her head, but she was too fucking fast. And when she stuck her finger up my back door, I unloaded a week's worth of accumulated cum in a few seconds. Well, maybe not a full week, because I had taken care of myself as I went along. I guess my balls liked her enough to make an extra batch for her.

I hoped she would choose to go to the Dining Room. I wanted to spend as much time with her as I could; there's plenty of time to fuck, but not enough to sit and talk and laugh and get to know someone. Oh, she's calling momma. Well, well. If any other girl had told her mother that she would be doing a full weekend with some guy she met in the Four Seasons bar, I would have told her to invite the mother over for a threesome.

This one I wanted alone.


"Put that shirt down. You said you felt grungy, or was that just a line to get me up here to your bed?"

"I'm sorry, but I really was anxious to sit across a table from you and hold your hands. I just forgot. The answer to both your questions is yes, I did feel grungy and yes, I did want to get you into bed. Since we're both naked, I can take the hint; let's take a shower now before dinner."

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Story tagged with:
Ma/Fa / Oral Sex / Anal Sex / Squirting / Water Sports /