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."

.... There is more of this story ...

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