99 First Dates Ch. 02

I told her that I had to run to a doctor's appointment, something to do with my growing deafness. She got the hint.

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42. One Brown Mouse -- She showed up for coffee dressed up all frumpy and she kept her eyes down and her mouth shut most of the evening. She was vaguely cute and with a bit of effort she could possibly be cleaned up and converted into a sexy librarian sort of gal.

I was willing to give it a try... the quiet ones are always crazy-hot once you get them into bed, but she didn't return any of my three post-date phone calls.

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43. The Swinger -- This wild gal in her early thirties alternately fascinated and repulsed me. She was pretty good looking but was showing her mileage a bit. She was an unashamed 'swinger' and admitted that she and her last ex used to go to swapping parties every weekend. He got tired of that scene -- she didn't, so they split. Her favorite way to spend a weekend would be to have ten plus guys all pulling a train on her.

Ok, I'm a pig and I must have had temporary insanity. I gave her the second dinner date and we bumped uglies all that Friday night. She was good enough in bed that we stayed there most of Saturday as well. Since all of my blood had flowed out of my brain and into my cock once again, I let her talk me into taking me to a private swinger party being held at a friend of hers that night - but I didn't stay too long.

She wanted to fuck other people, namely everyone else who was there, both male and female, and I soon found it annoying to watch. Oh, I got my rocks off with a couple of willing swinging wives, while their hubbies happily boned other equally willing swinging wives, but I personally couldn't handle the jealousy. I'm not really cut out to be a happy swinger.

After getting my rocks off a few times and watching my date get three-hole penetrated repeatedly until she saw heaven, I became bored, so I put on my clothes and went home. She didn't call me back and I had my family doctor give me a full sexually transmitted disease workup and I fretted for over a week until he said I was clean.

Never again!

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44. Ms. Yankee Independence -- I met her entirely by happenstance. Some friends of mine were having a big Friday after work get-together and everyone invited their friends and co-workers. We ended up with a crowd of over twenty people at one long table and six of them were visiting school teachers who had just moved down together from Massachusetts to work contract for our local school system. In the next three fun filled hours they proceeded to drink us guys nearly under the table.

Figuring we had been hoodwinked, the men were trying to count our money under the table to make sure we could cover the astronomical liquor bill. When the check came one of the women instantly grabbed it and with her calculator, quickly did the math to split the bill equally among everyone, and called out a number... and all the visiting teachers started laying money on the table!

I asked the guy next to me, "What the heck are they doing?"

He said, "I think they're paying for their own drinks!"

"No Way! I've never seen that happen."

"Me neither!" Said my friend in total awe and amazement. We thought those northern guys must have had it made!

I had a second and third date with one of these teachers but it didn't really work out. Too much culture difference and she knew that she wasn't going to stay down here for good, so she didn't want to get too serious into any relationship and then leave. We became friends with benefits for the next six months until she returned home and she didn't mind that I was continuing my disastrous trend of first dates with other women, and found my updates hilarious.

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45. The Professional Dater - She had dated over twenty different men in the past six months, but she 'just couldn't find what she was looking for'. She told me this on the first date. Obviously, much like Ms. Perfect, she was never going to find what she was really looking for... the quote 'Perfect Man', nor was she willing at the moment to settle for something less.

I wished her good luck with her virtually hopeless Diogenian search. As far as I know that old Greek is still looking for an honest man too.

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46. The Werewolf -- Honestly, she had more facial hair than I did!

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47. Hotty McHot-Rod -- She pulled up in front of the café driving a fire engine red Porsche Turbo Targa convertible and wore a screaming red leather mini-dress with designer brand sunglasses. She drank her latte and pointedly asked me what kind of car I drove! Since I buy/sell antiques and haul things about for a living, I proudly showed her my eight year old beat-up pickup truck and she soon left to burn rubber somewhere else. What an insufferable egomaniac!

In my opinion, and I admit that it's a minority one, cars are for transportation and functional utility, rather than status symbols. Sure beemers and BMW's are nice, but for me they're not functional... and I don't want the sort of wife that needs an expensive car as a necessary fashion accessory.

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48. Ms. Fitness Zealot -- Ok, her profile said she was athletic and very physically active, but I was a bit surprised when she ran the six miles to meet me for our coffee date. She sneered at my very slight paunch and couldn't drink her energy drink fast enough before she left to finish her 'normal daily ten mile run'. Good riddance.

I have nothing against skinny girls who can fit into a size 4 dress, or even a size 0 dress, but honestly this overly thin gal looked like a bag of antlers. I've seen men and boys with more breasts than she had and her hip bones that were well displayed above her running shorts looked dangerously sharp. She looked much too fragile to indulge in sex, besides; she'd probably always be too tired from her other workouts anyway.

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49. A Rebel without a Clue -- There are always some people that just have to do things their own way. She didn't just march to a different drummer... she had her old own alternative band playing inside her head. She arrived on roller skates... and I got the impression she lived in them pretty much all of the time. She admitted she wore them most of the hours of the day that she was vertical and she didn't seem to have a 'real job'. Not as many tats as Lydia, and she really wasn't as interesting as a person either.

She was angry and mad at the world and probably had been since she turned fifteen. She'd still probably be angry after she turned fifty. She drank her tea and we both mumbled apologies. No harm -- no foul.

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50. The Valley Girl -- Ok, she wasn't quite that vapid, but the way she spoke at dinner constantly put my teeth on edge. She was a stereotypical blond ditz and she constantly said 'like', yet not once ever in the correct context. You can tolerate teens that talk like that but by the time you're forty it just makes you sound retarded or drug addled. I'm not a grammar Nazi, but long ago some school English teacher should have tried to shake some sense into her. Fer sure!

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My staff was having much too much fun with my dating disasters by now. They now posted the wagering board openly in the café so that even our customers could enter into the bidding. The winning jackpot for picking the winning date number was currently at over a thousand dollars!

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51. Ye Olde Towne Bicycle -- This amazing woman was a walking and talking advertisement for eugenics or forced sterilization. She had, I kid you not, thirteen kids by nine different daddies... several of the fathers were of course 'unknown'. She couldn't even keep track of all of the guys who had nailed her in just the last two weeks! Apparently every guy in town had already screwed her except for me! Talk about taking someone else's sloppy seconds! She even joked about wanting to push out a few more crotch-fruit. Not with my dick!

I don't know why she was even selected as an option for a first date. I checked her profile later, and she had no kids listed. Why do they always pull that shit? Do they think that men are that stupid that they can just flash some tits and our brains go to mush? Well, sometimes... but not this time.

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52. The Sociological Experiment -- In an odd sort of way I was kind of amused with what she did. She set about to intentionally try to find and then push any or all of my emotional buttons, just to see how I ticked and what it took to piss me off. It was all a grand experiment on her part to see how much she could push me around and still get away with it.

Two can play that game and she left in tears less than forty-five seconds later. I only commented to her that she looked a lot like her sister, with whom I had been having an affair with for nearly ten years and I now wanted to 'complete my collection', preferably with them both chained up in my secure and soundproof cellar dungeon.

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53. My Plastic, Non-Fantastic Lover -- This date can be summed up by just two words - Fake titties. Somewhere along the line she had installed some monstrous implants into her chest. She now constantly wore low cut blouses so she could made sure that everyone could admire her new augmented tits properly. She also complained about new lines appearing in her face and she asked me if she should also get butt implants? I sarcastically told her she should wait until after I'd fucked her current ass first to see if it needed more cushioning.

Amazingly, she took that as a compliment and handed me her house keys so I could immediately give it a proper deep probing inspection. I did, and it really wasn't worth what I'd anticipated.

I'd never fucked a woman before with huge breast implants and I just couldn't resist the opportunity to broaden my education. It was so not worth it. She was like a limp dead body in bed and I had to do 99% of the work. Fake tits aren't nearly as delightful to feel, nuzzle, lick, kiss, bite and caress as real (natural smaller) ones are. Live and learn.

To end the affair, I mentioned that she'd soon need another facelift and she screamed bloody murder and booked the next flight out to Beverly Hills, California.

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54. Ms. Un-Domestic -- There is a little bit of Elvis in every man (except for Michael J. Fox who is the Anti-Elvis, but that's someone else's long story) so accordingly, there ought to be a little bit of Julia Child in nearly every woman, except for this one. I soon found out that she could just barely boil water let alone actually cook anything. She seemed to live on Raisin Bran cereal for meals in which she didn't eat out or nuke a frozen dinner in the microwave. I swear, I've seem seen more actually food in a male college dorm room refrigerator than what she had in hers. Oh, and she didn't clean house either.

Ok, I'm a decent cook and I didn't actually require a gourmet chef for a wife, but she had enough other minor faults and eccentricities that when they all added up all together they spelled long term trouble. Her finances were also a complete mess and most of her credit cards were close to maxed out.

I'd been in that sort of mess once before, no thanks.

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55. The Vegan Zealot -- Just the memory of her brings a shudder. She was way beyond being just a vegetarian and she turned it into a complete lifestyle. She wanted the dinner option, but it was a crime against nature with what the head chef had to do to prepare her a meal that would meet her insanely strict standards. Living that way just makes finding restaurants we could both enjoy way too hard, and agreeing on anything that we could share together became practically impossible.

I dropped her off at her home after our very awkward dinner, but first along the way I stopped at a Wendy's to buy myself a double-Baconator cheeseburger. She was suitably horrified, much to my obviously transparent malicious delight.

It's weird how many vegetarians hate salads, btw.

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56. The Crazy Cat Lady -- Ok, she thought we'd be good together because we both loved cats. I have one, an addled and not very bright but loveable longhair. We went after coffee to go see her cats and I was astonished to find that she currently kept about thirty cats inside her house... peeew! The cat box odor was nearly overpowering and I coughed nonstop the entire five minutes I was there.

I then falsely admitted that I also kept a pair of large voracious Rottweiler dogs and her ardor for me cooled markedly.

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57. The Animal Hater -- She was pretty, witty and had a wonderful sense of humor... but she didn't like animals at all, either cats or dogs... or fish, birds or turtles. My cat is really my very best friend. If you can't be around him without flinching or cringing, it'll never work.

She made an ultimatum after the second date, either the cat or me goes... guess which went?

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58. Ms. Workaholic - She postponed our first coffee date on two prior occasions due to having to stay late at work. I understood that -- stuff happens. The day that she finally showed up she brought along her work laptop and tried to multi-task her current marketing sales plan while we talked.

Too bad. She was not bad looking but it was quite obvious where her priorities in life were. I was always going to come at least a very distant second place in her thoughts, let alone her heart.

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59. Ms. Priss -- She demanded the dinner date, arrived there nearly forty minutes late, and then decided that my favorite local Italian joint wasn't nearly good enough for her. We compromised on a local up-market bistro where I overpaid for a pair of dinners that each barely looked adequate for being labeled as an appetizer. Then she picked at her food for over an hour. She looked and acted high maintenance - very high maintenance.

Some guys look for that sort of woman. They are looking for a trophy to be seen with rather than a real relationship, but I don't have the temperament or the patience for that sort of thing.

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60. The Former Stripper -- Ordinarily a former stripper would be just a great one date dame, but she was so much fun to be around that I asked for seconds. I took her out for a nice dinner and later that night she took me for a trip around the world in bed.

She had just enough issues and drama surrounding her that I (reluctantly) decided that she wasn't a good long-term fit... so she then hooked me up with her roommate!

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61. The Roommate -- Her roommate was still a stripper... and was another great gal when out on a date. I picked her up from her nightclub at 2:30 a.m. and then we chatted like old friends at a local coffee shop until dawn. Then we went back to my place where she also took me all the way around the world in bed... twice.

She loved her job (stripping) and intended to do it until her tits fell off, or she'd made enough money to retire in comfort for the rest of her life. She wasn't looking for any full time boyfriends and I didn't want everyone looking at my girlfriend's bare tits and smoothly shaved cunt. We decided to stay friends with benefits.

When I took her home the next afternoon, she, her roommate and I somehow all ended up back in bed together.

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62. The Stripper + Her Roommate Together -- Does this count as a second first date????

I made a note to myself afterwards that having a very bisexual girlfriend or wife would definitely keep things from ever being dull in the bedroom!

The Stripper soon got a better job offer at a bigger club in another city and both gals then moved out of town, but the going away party (with a few more of their female friends) ending up being legendary. I was exhausted, but I had a stupid happy smile stuck on my face for most of the next week.

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