99 First Dates Ch. 03

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Stultus
Stultus
1,400 Followers

85. Sharpie McEyebrows -- This coffee date was absolutely no fun at all. She kept a constipated expression on her face the entire twenty minutes we met. Her makeup was just well... disturbing. I suggested that she quit being a killjoy and instead she should go pluck her eyebrows into even further oblivion.

I then discovered to my horror that she had received 'permanent makeup'. In fact, her eyebrows had been permanently laser removed and replaced with a less than realistic tattoo. Same also for her overly bright eyeliner, cheek blush and lipstick.

Shudder.

*************

86. Ms. Social Butterfly #2 -- I wondered if she had ever met the other Social Butterfly, if so they were undoubtedly hated rivals. She also ran a complete nightly schedule of appointments scheduled often weeks in advance, but with future planned dates. Apparently, she couldn't ever tolerate being alone by herself for even a moment.

I quickly decided that the further away I kept myself from her, the better. She was showing unhealthy interest in organizing my own schedule. I told her that I was late for an amateur porno film shooting and went to go visit The Nympho Slut.

*************

87. Miss Princess -- She wanted the dinner and the full roses and violin treatment. She even expected me to pull out her chair for her. Her tiny little evening sequined clutch handbag contained only some lipstick, a little compact of coverup and a handkerchief. She acted like she was made out of porcelain, but she wasn't nearly as entertaining as a good old piece of antique Dresden fine china.

My follow-up advice for ladies that constantly act helpless, just like an anti-bellum Southern Belle straight from a plantation, is that men will see you as somebody who expects to be constantly taken care of. That may be a turn-on for some guys but it's a big turn-off for many others, like me. If you want a guy to constantly take care of you, don't be surprised when he doesn't treat you as an equal in the relationship.

*************

88. Ms. Social Butterfly #3 -- Fuck! How many of these sorts of women are out there? This busy gal always spends most of her evenings out with her girlfriends. A couple of drinks after work, bridge night, movie night, pottery class night, and art night at a gallery or museum, and of course long Friday nights at their favorite bar. It came as no surprise at all however that my usual one night a week out with the guys was going to be a big no-no for her. Go figure... what was good for goose was apparently not at all good for the gander.

It was even less of a surprise to learn that all of her friends had multiple divorces between them. Unspoken was the impression that her own previous three failed marriages had resulted because she spent more time and emotional energy on her friends than on her husband.

Also, any group of women that hit the same bar every single Friday night are usually looking for more than some bar snacks and to pound down a few glasses of cheap Chardonnay. They apparently wanted the right to have a little fling on occasion whenever the mood suited them.

Obviously this was trouble just waiting to happen. I decided to go home and add to my collection of Internet porn and wrangled a last second date with Rosie Palm and her four sisters... The Nympho Slut and I were finally on the outs after I discovered she'd posted some of our sex videos on YouPorn.

*************

89. Ms. Feminist Zealot -- Have I mentioned how much I hate all zealots? This one was a radical liberal who blamed me as a man and my lifestyle for destroying the entire planet... but for some reason she was convinced she could save me! She also exhibited extreme hardcore-feminist leanings that were going to be awfully hard to live with. She left the dinner table fast when I suggested the greatest punch ever thrown in professional boxing was when Mike Tyson beat-up his first wife. That was really cruel, but she was prodding on my last nerve.

Equality in a relationship is fine. One partner being just a little more equal than the other sucks, and I'm not dealing with that ever again.

*************

90. Ms. Social Butterfly #4 -- Where do all of these desperately and pathetically lonely women come from? This one usually spend two to three nights a week out doing the elite social scene with the top movers and shakers of the city. Boy was she ever disappointed that I wasn't a millionaire and didn't even have a boat, let alone a yacht.

The less I say about her cult worship of certain far, far right wing fringe politicians, the better. Also her rabid gushing about her religious cult at the prestigious First Baptist Church nearly qualified her for the Zealot of the Year award... until I met a woman even crazier a few weeks later on.

*************

91. The Freak -- This poor gal actually made The Doormat look sane and well-adjusted. Really!

Trust me. I don't want to hear about your love for autoerotic sexual role-playing games, like being fake raped and nearly (but not quite) strangled to death with your own pantyhose. The fact that you need sharp intense pain in order to achieve orgasm is not first date material, even for me!

I decided to reuse the line about her bloody dress being marked Exhibit A on my bedroom floor, but it didn't frighten her off in the least. I then ran for Farah's help in getting this poor woman out of our café and well out of my life.

Alarmingly, I had at least three friends push me rather hard for her name and phone number. I didn't give it to them... I really didn't want to hear about any more details of her extreme sado-masochistic sex lifestyle.

*************

92. The Professional Paranoid -- She was suspicious of everything I offered her at our coffee date and had Farah replace her coffee often so that I couldn't secretly drug her and then 'date rape' her. What a total nutcase!

The 'run screaming for the hills moment' was when she commented that she knew a lot of people who were kiddy-diddlers. In fact, every man she meet seemed to turn out to be one. I didn't like the way she then looked at me. It had 'YOU'RE NEXT' written all over her.

I told her to go away, that she was much too old for me... but could I see some cute bathtub pictures of her grandchildren?

Yes, she called the police on me, but I let Farah straighten them out. They already had her on their 'rubber room' list, as she phoned in several complaints about kiddy-diddlers running amok on the streets each and every day. Not one of her complaints had ever been even remotely substantiated.

The cops loved our coffee and pastries and within a week the local district station officers were coming in every morning and often late at night for their caffeine and sugar fixes. The safest business in the world is one that quickly gets the reputation of being a cop hangout, even when they're out of uniform. One idiot tried to stick up Farah's new husband several months later late one night and three off duty cops quickly had him covered. No one ever tried it again.

*************

93. Ms. Oblivious #2 -- Like the original Ms. Oblivious, this gal was darned near utterly clueless about anything around her... and nearly a hundred pounds overweight for good measure. She imagined herself as some sort of fairy princess, and like the Princess, she wanted the full treatment with nothing but the very best and lots of attention. But when she got up to powder her nose and knocked the chair over with her huge ass, she never noticed that I leaped and caught it... or pushed it back in later for her massive backside. Nor did she notice when her fat rump bashed into a dozen other chairs both to and from the restroom.

If she noticed anything that occurred in life past her nose, I seriously doubted it. She certainly didn't notice the dinner check and pointedly looked away when I started to loudly and obviously calculate a tip to give our waiter, whom she'd abused the entire dinner.

*************

94. The Compleat Zealot -- Yes, the archaic spelling is intentional. This zealot took the absolute top prize for being fifty pounds of crazy in just a ten-pound bag. She was so horrifying that it was just like a snake mesmerizing a mouse, I just couldn't look away. She was also quite as cute as a button and had a pert ass that I was longing to sodomize.

Over dinner, drinks and two rounds of desserts, she tried to convert me at the first date to become a vegetarian, bicycle pedaling, democrat, and attend church with her on Saturday at her wacko new-age cult church where they talked to crystals.

She was such a magnificent train-wreck that it really hurt my conscience to inform her that I was a meat gobbling, truck polluting, dyed in the wool political moderate (everyone hates us). When that didn't faze her I then complained that the Catholic Church had really gone off the rails into heresy since the unfortunate reforms of Vatican II.

I hinted, loudly, that I'd be more than willing to take her back to my place to discuss peace, love, mutual understanding... and a lot more love. Preferably physical. She smiled but said no, and her pert ass wiggled off un-buggered.

*************

95. Ms. Indian Brave on the Warpath -- If just a little makeup really brings out the beauty of a woman, then a ton of makeup donned with a trowel must be even better, right? Not hardly. She wore so much makeup that I have no idea what she actually looked like underneath. She proudly stated that it took her two hours to do her 'normal' everyday war paint and an hour every night to remove it.

Way too high maintenance.

*************

96. Ms. Toilet Mouth -- Hey, I admit that I often swear like a sailor and don't mind a lady with a bit of an earthy mouth who can talk dirty to me in the bedroom, but not every other word out of her mouth, and not on a first date... and not loudly in a family café.

Since she clearly knew what the word 'fuck' meant (she'd used it at least once a minute our entire date), I suggested to her that we quit the fucking pussyfooting and go back to my place to do some real fucking. Not surprisingly, this offended her and she slapped my face and left.

Honestly I was a bit disappointed that she didn't say 'sure, let's ball!' She wasn't that much of a looker and didn't possess any long term qualities suitable to a relationship, I did had to admit that I was curious to find out how nasty I could get her talk in bed.

*************

97. The Compulsive Hoarder -- Ok, I'm pretty bad about buying and saving old junk. My shop is full of it and my house used to be full of it. Don't even ask about my still over-stuffed garage. But she was even worse than I was. She kept all of her trash saved up in bags in the kitchen by the back door for weeks, if not months. There were even more, older, full trash bags sitting against the house outside. Just in case she decided she needed to retrieve something back from the rubbish.

It wouldn't have surprised me in the least if there was a long dead relative still buried under heaps of trash somewhere in that house. Cringe.

*************

98. Not Being Jane Austin -- I couldn't believe it when she said that I simply failed to measure up because I wasn't a proper Mr. Darcy in the flesh. Just where did I put those knee-breeches and long waistcoat? The fact that I could in fact recite from memory the entire plot of Jane Austin's 'Persuasion' unfortunately didn't redeem me in her eyes in the slightest.

She really got up my nose, so I asked her when I needed to drop her back at Refuge Pines, a noted local private bughouse for the terminally demented.

*************

99. The Sports Widower -- I knew she liked sports... a lot, but it is not a religion for me. I'm rather partial to baseball and I don't mind watching our local pro football team lose (usually rather badly) but my life doesn't revolve around professional sports. Instead of a dinner date, she requested a date at the local ballpark. Well, that night at the ballpark ended up costing more than most dinner dates and then at the very end of the date she announced that she was a confirmed Lesbian.

Damn it! She had scammed me! All she had really wanted was to score some nice tickets to see the game at someone else's expense. I did a little research and found that she had pulled this scam on at least three other gents at our dating service. We compared notes and then filed complaints and she was kicked out of the dating service, but I still see profiles very similar to hers still running on Craigslist. Caveat Emptor.

*************

I was now way more than just seriously pissed!

That was the last straw, I raged at everyone who would listen! The doomsday clock on the wall was going to stay stuck at 'Now Serving #100' because I was done with dating.

Done -- finished -- fini!

I was over and done with dating - for good. Frankly by this point in my life, I would have been hard pressed to thing think of anything nice to say about a woman, let alone select any of their allegedly fair sex for a long and very meaningful relationship.

No More!

*************

This attitude lasted for about a week, and then the love of my life walked into our café.

I was working one evening at cleaning up some old Chinese jade snuff bottles to make them ready for display in a showcase when I looked up suddenly into the eyes of sheer perfection.

"Farah says that you've gone off women... for good. Are you going to go bat for the other team now and chase after buff hairless pool boys? You do tend to look at women's asses more than their tits." The divine creature asked.

I stuck my tongue out at her and blatted.

"Good stout and brave fellow! Once more into the breech! Besides, I've got a few hundred dollars invested in your dating pool, so get off your cute tight ass and go make some romance!"

"Bah! The world, or at least this section of it, is remarkably short of suitable, attractive women of indeterminate years looking for a sane, reasonably normal and fairly well-adjusted relationship. Beside, my friend Antonio at my favorite Italian restaurant says he's suffered enough property damage and has promised to chuck the next woman I bring there into a dumpster."

"That would be a terrible shame, because Tony makes my chicken piccata just exactly the way I like it and he has never once complained about my dining habits. Tonight I'm in a lasagna mood though. Now see what you've done! You started to talk about food in front of a hungry woman and now I'm starving! It's all your entire fault... but to make up for it, I will allow you to make take me out to dinner. Are you ready to go? Besides I think that snuff bottle is actually soapstone and no amount of polishing is going to improve it. It also looks like a later Victorian era reproduction as well, but I'm sure you'd already noticed that."

I hadn't. That was worth the price of dinner and then some!

*************

Our dinner date would have been a dream, except for the odd disfunctionality of the entire experience. Antonio not only was delighted to see me enter his restaurant with a new date, but he fixed up a special table for us with his best glassware and his finest Italian wine!

I should have smelled the rat right from the start!

By dessert, when he declined to offer me the bill for payment of this magnificent feast, I knew the fix was in... especially when Antonio came over to give his niece a big hug and kiss. I'd been played and 'scammed again' - but in a delightfully different and nice sort of way.

Besides, I'd already been in head over heels in love with her since the garlic bread first arrived at our table, long before our lasagnas arrived.

Even dressed casually, she was a creature of beauty and elegance. She was cultured and very well educated but never wore it like a suit of armor. Her father, Antonio's brother, was in banking and her mother had been a Charleston, SC socialite. Obviously she had money, but she didn't flaunt it. She had many hobbies and interests, including antiques and owned and operated her own antiquarian bookstore. It was also quite clear that she had a wild sense of humor, a natural love of adventure and fun, and a perhaps a rather checkered past of intimate wildness with very unsuitable men, like me.

"So," She asked me with a laugh, "what exactly were your qualifications for your future intended girlfriend?"

"Oh, the usual small little things that every man looks for. A bisexual gourmet chef from a filthy rich family that looks good in stiletto heels and a set of pearls... and nothing else, and enjoys lots of quality time spent with her lord and master... mostly on her knees or all fours. Just the usual tiny things necessary for domestic bliss."

"Oh dear, I'm badly over-qualified then. I loved to diddle my best girlfriend at my private finishing school and my college roommates and I shared many wonderful hours with a rather special double-ended dildo on weekends when we couldn't get otherwise laid by prep school boys or outlaw bikers from ear to ear. My mother did send me to a famous cooking school in Connecticut after college and I've learned some really nasty fun things that can be done with really good chocolate mousse in bed while wearing seven inch pumps, but it makes the pearls hard to clean afterwards."

"I defer to your superior expertise then. Your resume for the very vacant position seems quite in order!" I laughed.

"Quite," She agreed, "but that's not the point. Now we'll see if you match my currently current qualifications... but on the other hand, I do also have an opening for a swarthy pool boy, if all else fails."

*************

For the next two weeks she played the game of 'hard to get' down to perfection. She knew just how to keep me stimulated and primed for the chase after her. I'd call her pleading for another date but she'd always put me off... but in a very carefully calculated sort of way that sounded 'reasonable' and not too ego deflating. I'd grumble and be an utter bear to deal with at work for a few days and then call her up to try my fortune again... and then later yet again.

Finally when I got that second date, it was just as good. She dolled herself up a bit and wore her lovely long rusty brown hair up into ringlets that teased the bare shoulders of her spaghetti strap dress. She didn't wear the full seven inch heels, but she carried herself like a goddess in the more mundane four inch ones. This dinner at a nice seafood restaurant I was allowed to pick up the tab, but she offered to pay the tip. I declined to let her, this time.

Getting that third date took me another two full weeks of near pleading effort, but it was worth every moment of the wait. She wore an utterly amazing silk halter gown that was nearly backless almost down to her ass, and it showed off the glories of her flawless front cleavage to perfection. I'm still not entirely certain how she kept all of the important parts of herself covered. I spent the evening agog at her splendor and probably spilled about half of my dinner into my lap because I too agog with wonder to eat or chew properly.

Stultus
Stultus
1,400 Followers