99 First Dates (Revised) - Cover

99 First Dates (Revised)

Copyright© 2010 by Stultus

Chapter 2

Humor Sex Story: Chapter 2 - George is happily divorced and even more happily involved in his prospering business, but his friends think it is long past time for him to get back into the dating game once again. Hilarity ensures. Gently revised to fix typos.

Caution: This Humor Sex Story contains strong sexual content, including Ma/Fa   True Story   Humor   Slow  

The litany of romantic horror continues...

18. Ms. Stuck-Up Bitch - I've had first dates where the woman was rude or snide or otherwise disagreeable, but never to the extent that this woman demonstrated. If she had anything nice or pleasant to say during our brief coffee date than I must have blinked and missed hearing it. She made especially rude comments about Farah and loudly wondered why 'those sort of people' were being allowed in this country. I wondered if this is how she always acted on a first date when the rest of the world tries to put their best foot forward? Or maybe this was her best behavior?

Yikes. Either way, no second date.

Later, she griped to all of her friends about what an awful date I was, like I was some sort of player or sleezebag because I didn't call her back, and via a friend of a friend, the word of her displeasure came to be known to me. I'm a bit of an odd sort of fellow and many of my friends are even stranger and odder still. A good wife would need to be able to treat them well, because I'm not certainly going to have you around for a moment if you're going to habitually hurt my friends' feelings.


19. Ms. No Goals - She was pretty enough and she had a bit of intelligence, but otherwise she displayed a complete and utter lack of any meaningful ambition in life. She didn't have a single life-goal past getting married. What a waste. She didn't even seem particularly concerned that I wouldn't be asking her out again.

All that sort of behavior and attitude tells me is that you can't wait until you can sit at home all day watching soap operas and reality TV, getting fat and leeching off of my income.


20. The Martha Stewart wanna-be - The coffee date went so well that I tagged her for dinner the next night. That went alright too and then she invited me to her house for dinner the following night. Everything in her house was picture perfect ... and god help the man who put anything out of place! She could cook like a dream but I could already watch her knuckles turning white whenever I moved or touched anything or didn't keep things exactly as she wanted them. She wanted a curator for her domestic museum, not a helpmate and partner in life.

I had seconds on dessert and started to think of suitable ways to break our association. The quick and simple method was to let her see the pig sty that was my apartment on our next date. Ok, I deliberately didn't do dishes or laundry for a few days and tossed a few things around (I'm not a complete domestic disaster) and let her panic. She nearly immediately created the few small suitable lies that ended our relationship on a mutually satisfactory note.


21. Ms Perfection - A smug condescending woman who let me know in the first minute of our conversation that I wasn't at all up to her normal standards, but that she'd try and stoop down a bit closer to my level and give me a try. She was nearly forty years old herself, never married, but believed that she was the finest piece of ripe fruit still hanging on the tree.

Hey ladies, if you're going to have a take-it-or-leave-it attitude, most guys (like me) are going to choose option B.

I predict that she will still be unmarried in another ten or twenty years, but that her standards wouldn't have declined in the slightest. It would never be her fault that no man was capable of being worthy of her.


22. Ms. Bored - This woman confused me to no ends. She acted bored out of her skull with a 'why am I here?' look on her face and yawned all night long when she was with me ... then complained bitterly to me when she called me a week later to gripe that I hadn't called her back to ask her out for another date!

I chalked it all up to her living in a slightly different reality than mine and I gave her a gentle letdown.


23. The Ms. was a Mrs. - Being already married is a serious deal-breaker for me, but from the way she was playing footsie with me under the table, I guessed that finding out later on after we had had sex would be an even worse way to find this fact out. I don't do adultery, so yeah, I guess in that way I respected her candor by admitting the truth upfront. I think she would have been fun in bed, but I didn't want any sort of scene with an outraged husband, or his firearm collection.


24. A Dinner for Three - It was supposed to be a quiet intimate dinner for two, but all night long there was another man at the dinner table. Figuratively speaking anyway. She was tall, bright and beautiful, but all dinner long she kept mentioning her ex who now lived in Colorado and how she was looking forward to seeing him again when he returned home here in a few weeks to visit his parents.

No bets but what she wouldn't run back into his bed the moment he crooked his little finger at her. This also smacked of drama, and I didn't need any in my life.


25. Ms. Secretive – She was almost the perfect woman; bright, intelligent and hot looking with gorgeous hair, perky breasts I wanted to inspect at close hand, and her smoking little black dress showed off a lot of nice soft and creamy thigh. I also never learned one single thing that was true about her - and her phone number and address were both false. Was she CIA, MI:5, or some other spook? Or just another crazy gal playing mind games? She then disappeared without a trace, with all of her on-line information now gone.

I waited by the phone for her to call me back for several weeks but she never did.


26. The Flirt - I like a perky woman and don't mind it a bit when they get a bit assertive or aggressive, but not with other men while on a date with me. She flirted non-stop with every waiter/busboy/or other male that passed within ten feet of her. I really didn't like the wink she was giving to another male restaurant patron who was trying to ignore her and pay attention to his own date. It didn't work. Outraged, his date upended a mostly full plate of pasta over his head and stomped out. The Flirt just winked at him harder and gave him one hell of a 'come hither' look.

I walked out too and told my old friend the waiter that my date was on her own and I left. Obviously she never noticed my absence and she just cast her net for other fish. Clearly she was not the sort of girl to remain faithful to just one guy at a time.


27. The Commander – Her Imperial Ladyship tried to give out the orders from the moment we met at the restaurant. She took full charge and ordered everything, even my dinner ... quite against my wishes, but she wouldn't take no for an answer. She drove our waiter half-crazy, running him back and forth non-stop for the entire meal and treated the menials with the scorn that she obviously thought they deserved.

By the time the check comes, I already know if I'm going to ask a woman out again. One of the most important things I look for is how she treats the wait staff. I think that this is a very fair test. I've even given the waiter/waitress a bigger tip if my date was being a bitch to them. I have no time for inconsiderate people. It's more about rudeness, really. It is the same as with the cell phone behavior, an 'I don't think you're important enough to pay you the same consideration you're paying me' kind of thing. Luckily, these types of people are easy to discover as they're also usually the same kind of folks that think it's ok to treat their servers like boot scum. So they're not exactly hard to recognize.

I had to make a fast break from this man-eater the moment dinner was over. Given time, this Hunting Girl would have had me licking her boots with my tongue and polishing her saddle leather while she gleefully sodomized my virgin ass with her riding crop. Kinky, but not the sort of refined acts that get my juicer harder than nun's buns. I did give a rather odd sort of wimpy friend of mine her phone number and they've been an item ever since. The world is full of all sorts of different types of peope.


28. The Mushroom – She was pretty in a mousy sort of way, but she was even less motivated than Ms. No-Goals. She had no interest in the outdoors or really ever leaving her house to do much of anything. She didn't even like shopping. Fortunately she had a computer programming job where she could work from home most days and never leave the house until she ran out of Haagen-Dazs or Dove bars, and mostly she didn't. I gave her a couple of tries but she never wanted to do much of anything, and we'd always end up watching a Netflix movie at her home. I'm pretty sure she was borderline agoraphobic but she said she was happy with being a homebody.

She also had a sex drive of almost zero and pulled back hard anytime I tried to go past first base. We sort of stayed friends, but without 'benefits'.


29. Miss 'Thang' – I didn't believe it was possible but I met a woman even more self-absorbed than Ms. Perfect above! She had the attitude of 'my shit don't stink' permanently carved on her face. It was ME ME ME ME ME ME all night long. Utterly and completely self-absorbed. She also probably never even noticed during our coffee date when I said goodnight and left her blabbing on.

It's great if you talk about yourself on the first date, cause we're getting to know each other and all that, but if I'm sitting there wondering when you're going to shut up the fuck up, and you're ten minutes in to your diatribe about how much you love watching Desperate Housewives, then the relationship isn't going to go anywhere.


30. BPD #2 – This one nearly traumatized my entire attitude towards meeting any more strange unfamiliar women. She threw her cup of coffee at me just because I mentioned that I occasionally liked to hang out with a few of my buddies once in a while. She then threw a chair at me when I mentioned that I didn't think we ought to see each other and the police had to be called. She had a long police history of exhibiting bizarre behavior and apparently she had gone off of her medications. They packed her off to a county mental hospital where they kept her in a padded room for about five months. She turned up at the café again right after her release, once again off her meds and began raving about all of the letters I had sent her, begging for us to get back together again. We called the police again and she's back in the farm once more. She just refuses to take her meds. Absolute insanity!


At this point, with the thirty date bet mark met and about to be surpassed, our café staff started into some really serious wagering. The betting now ranged out to at least fifty dates as the new average estimation for how long it would take me to find an actual serviceable girlfriend, and they started to prominently keep track of my failures on the staff bulletin board.


31. Another Religious Nut - She turned out to be a Christian Taliban zealot who was too tightly wrapped up in her very personal relationship with God (capital G) to spare room in her life for any mere mortals. Some of her viewpoints about enacting religious laws as the future legal law of the land were frankly scary. She literally wanted to bring back stoning to death sinners who blasphemed against God ... or any of his thousands of other Laws. We politely agreed to disagree and had an interesting discussion about the Old Testament Book of Ruth, and she peaceably parted with me unconverted from my evil heathen ways.

Okay, I didn't expect to end up in bed on the first date, but when you start trying to convert me to your religion, because your religion is the most important thing in your universe, that pretty much eliminates any possibility of a second date.


32. Ms. Oblivious – I actually liked her quite a lot. She seemed smart, fun loving and had a good job that she enjoyed, but somehow the two of us were always a bit out of synch. She would always pull-back if I leaned too close and she didn't seem to like to be physically touched at all, even when I offered to help her with her coat. After three dates without even a single kiss goodnight I called it quits. She then called me a few weeks later to sincerely ask why I never made any sort of move on her?

It wasn't due to any lack of trying!


33. Ms. 16 Tons of Emotional Baggage - Thank goodness for it only being a coffee date. She poured out her soul to me as if I were her paid psychologist. Nothing apparently had ever gone right in her entire life and even her issues seemed to have issues all of their own ... mostly concerning her bad relationship with both of her parents.

Oops, sorry ... I have to run to an urgent appointment at my dentist. Elective root canal surgery that suddenly now can't wait. I'm too old to deal with 'daddy' issues ... but the very next new date had her issues in spades!


34. Ms. Serious Daddy Issues – A scary, scary woman. She was really a little too young for me but she was decent fun at dinner, even if she did talk about how important her father was in every other sentence. She wanted to see my place afterwards and her tiny thin dress hit the bedroom floor two minutes later. She wanted me to call her 'my little girl' or 'Angel' while fucking her ... while she called me 'Daddy'. Freaky!

The moment that we were done screwing, she then grabbed her cell phone to call her darling Daddy to tell him that she'd be late getting home, and then proceeded for the next twenty minutes to tell him all about her day. The really creepy part is that she wanted me to fuck her ass right then and there, while she talked on the phone with her father! Ok, she did like it up her butt, but that scene was seriously weird!

I didn't call her for a second date and she apparently found some other more willing daddy surrogate.


35. Ms. Impatient – During our casual coffee date she talked endlessly about marriage and having babies as soon as possible. She then complained why none of the previous men she had dated lately had ever called her back for a second date. I don't think she quite realized that this sort of talk (especially on a first date) tends to run men off pretty quick. Myself included.


36. Ms. Complainer – One of the worst dinner dates of my entire life. She complained about my appearance, didn't like the first two tables we were offered to be seated at, demanded that her fork be replaced, and then later her knife. When the dinner came sent her steak back to the kitchen twice, complained about the tomatoes in the salad, and just about everything else as well for no particular reason. I swear she had more gripes than the battleship Arizona! For dessert she whined and complained about the weather.

I have my own problems ... I don't want to hear about yours on a first date.


37. On the Rebound – I rather liked her, but she was just straight from a bad breakup/divorce and she was still in that 'hurt/mistrusting/angry' phase. I've been there myself. In another six months to a year, she'd probably be a bright happy and cheerful woman once again ... but not today.


38. The Drama Queen – From the first five minutes of our coffee date, I could feel the emotions rising. Virtually everything in her life was a disaster; in fact she was the living embodiment of 'management by crisis'. Apparently everyone at her work was an idiot so she had to do the work of five different people single-handedly, and her life at home wasn't any easier. Something was always needing her constant attention or one of her friends absolutely must have her advice or help with a project, since they couldn't do it themselves properly and only she – Wonder Woman, could do it right. And so forth. The icing was when she openly discussed her prozac and valium dependency.

Fortunately, a friend desperately needed her shopping advice and she had to rush off to once again save the day! I was about ready for a valium myself by that point and I needed about three glasses of red wine afterwards before I could chill out.


39. The Pathological Liar – I'd never heard so much bullshit before in a single hour. Her father was a famous professional baseball player (who didn't appear for some reason in my current edition of the Baseball Encyclopedia); She also claimed to be a cancer survivor of a rare near incurable variety; had been raped repeatedly back in college but the cops laughed at her because the man who did it was someone famous. She has restraining orders against three different men that have been stalking her for years; and of course her family was wealthy and has houses all over the world. You get the idea.

Complete and total bull shit!

For paybacks, I told her that I was an escapee from a Mississippi chain gang and that I was hunting for my missing partner in crime who had legged off with seven million dollars in uncut diamonds from our last heist. She sounded intrigued, but I told her I had to hoof it off to Mexico pronto ... after fitting my ex-partner into a shallow grave.


40. The Empty Dress – In my lengthy dating experience, I met several rather hot looking women who had, literally, nothing going on in their lives. They had cruised through life entirely on their looks. They don't read books or a newspaper (except to see if Macy's is having a sale). They don't understand ANY references to current events, politics or even history or literature. Their total sum knowledge of the world is whatever was happening within their circle of friends, going back about six months, and the latest reality TV celebrities.

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