Chess Ch. 01

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Autobiography - understanding women?
5.2k words
3.91
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Part 1 of the 3 part series

Updated 06/07/2023
Created 01/29/2016
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justbobkc
justbobkc
678 Followers

This is basically all true autobiographical stuff - but I've changed a few things like names and specific places to protect the innocent. I've also changed a few ages to conform to proper standards.

*****

Chess is a game invented to help teach principles of structured conflict and specifically warfare in the age of cavalry and castles. It can also teach some principles of sexual power, conflict, and seduction in just everyday human life. One wins at chess by thinking ahead, setting ever more subtle traps and employing ever deeper levels of subterfuge. And actually it is subterfuge in plain sight - as the rules are fixed and the board and moves are plainly visible to all. But "Jedi Mind Tricks" CAN come into play (at least among human competitors.) The Russians call this "maskerova" and employ it as a core principle of both warfare and intelligence activity. Not that this story has anything to do with Russians.

So - what does it mean when the most beautiful and sexiest woman in the office wants you to teach her how to play chess? We were already friends, or at least friendly. Her name was Diane and she lived with her boyfriend. We often went to lunch together and generally with her BFF - Jackie. Jackie had previously been a Playboy Bunny, then had gotten married but that didn't work out for her and she was currently going through a rough divorce. Now she worked for IBM as merely a secretary in one of the St. Louis Marketing offices, like Diane, despite her own obvious great looks AND already having a BA degree in some Humanities. But even Jackie wasn't quite as stunningly beautiful as Diane. Diane was about 5 foot 4 inches tall and weighed about 110 lbs. max. She looked to be about a 36C with a very thin waste and the cutest butt that just had that natural wiggle whenever she walked by in her high heels. She was always dressed very nicely and certainly sexy - in the fashionable styles of 1975.

I also worked for IBM then (obviously) as an order entry clerk. It was a pretty good job for me but I was way down on the office politics and social totem pole. The actual Marketing Reps and their managers were top dogs, the Alpha males with much higher earnings and the aggressive personalities that successful sales people have. Next came our technical support professionals for the Marketing Reps - the Systems Engineers and their managers. Back then both Marketing Reps and Systems Engineers had to have already earned a minimum of a 4 year college degree and both attended the very same intensive one month IBM school for marketing basics before specialization training. Then on that pecking order scale were the admin folks like us order entry, accounts receivables, and the secretaries and our admin managers. I COULD make a career in IBM through admin - becoming a manager had possibilities for a solid middle class life.

I was married then still to my first wife Lynn - but our marriage was on it's last legs and I was increasingly more interested in other women - not that I expected other women to actually be that interested in me.

I was not even an "average" guy. Ever. I have experienced a lot of angst in my life just wanting to somehow LOOK average. I was only not quite 5' 8" tall and also small at about 140 lbs. I was only 27 years old in 1975 but already had receding hair and the beginnings of a bald spot. I also had a less than "strong" chin and always wore glasses. And a pretty bad case of acne all through HS and even into my 20's. And I didn't even have two normal, average, eyes. One had been damaged and scarred in an accident when I was 12 years old. Now it didn't quite track accurately and was always kind of weepy and I was effectively blind in that eye. Many surveys of women on "sexual attractiveness" issues indicate that most women rate a man's eyes as the first thing they really look at when first judging him - by looks. Obviously I lose that in comparison with every other just "average" guy.

But it wasn't ALL just negative "not-average" stuff for me. If anyone ever got past that just looking beginning. Despite my size I was always very athletic and physical. I could always run faster - and further - than most other boys and men. I was in the top 5% for that - and even right then in 1975 I was a "star" on our weekend office touch football games, and even competing against former college level football players who now were Marketing Reps for IBM. And I was also just mean enough with a touch of that "Napoleon Complex" I never backed down from ANYONE, as far as physical confrontations. I was also actually stronger overall than most other average men. I had beat a lot of ther HS boys my age in arm wrestling and informal wrestling - even though they were always taller and weighed more. Maybe I had a slightly more than average levels of testosterone and even adrenaline (when needed) which caused these athletic abilities - as well as the acne and loss of hair.

I was also smarter than average. Despite never being a "nerd" or bookworm, I finished in the top 10% of my HS Senior class of 400 rather easily - and pretty much shocked everyone when I scored in the top 2% nationally on the National Merit Scholarship Qualifying test. I got a nice little certificate and about 2 minutes of local fame for that - but only those top 1% folks actually got any scholarship money. Me and my lower middle class origins would have to handle college on my own. Luckily that accident to my eye happened on public school grounds and we got a little settlement of $10,000 for that which was my college fund and good for just about 2 years at the Univ. of Illinois, where I was accepted.

But I was already in "love" - maybe - I certainly was in "lust", big time. I met her just as I was about to graduate from HS in 1966. I was in the band all through HS and we had rented our local small town pool for a graduation party. Our school district had to go to a "6-3-3" system because of overcrowding and lack of buildings. So 9th graders were still in Junior HS and only 10th graders (sophomores already) entered our HS. At this party Eugene (my best friend) yelled at me, "Catch" and threw this very cute strange girl to me. Eugene already had a girlfriend and I don't know how he even got Lynn in his arms - but he threw her at me and I caught her and pretty much didn't let her go the rest of that night - and she didn't complain. She was 17 and had just transferred into our HS for her senior year.

I dated her the rest of the summer and we clicked right off. She wasn't the first girl I had "gone steady" with and I wasn't a virgin (barely) - but she was and was reserved about sex. We made out a lot and she was a great and enthusiastic kisser. I generally had my Dad's big Buick as our date car - with bench front and rear seats - and we spent a lot of time at local Drive-in movies or just parking on country roads. She wouldn't even let me touch her breasts for months. Finally, after she had just turned 18, after watching most of "Dr. Zhivago" at the drive-in one rather chilly fall night - she undid the top of her red velvet dress and let me touch, caress, and kiss her breasts. I took my own shirt off as well and we laid together like that, but she still wouldn't let me get to "third base".

I was a tad frustrated - but I just masturbated pretty much daily. (Another indication of a tad excess of testosterone, maybe.) My first real girlfriend had been Karla, who was also in the HS band as a saxophone player and my same age. I started dating her just before the start of our Senior years. I called her at the suggestion of another of my band buddies who had dated her for a while but then dumped her. We went roller skating on our first date and she seemed to enjoy it. I saw her quite a bit that summer and she taught me a LOT about kissing and would let me touch her anywhere. My own Mom told me about this time in her own rather direct way, "just be careful and always use rubbers." I told Karla this when we were at the Drive-in soon after that conversation and her eyes got all shiny and she said "have you got them?"

But I was SUCH an idiot, I didn't want to use condoms. I had overheard one of our rich playboy BMOC's (big frog in a VERY small pool!) brag to one of his jock friends "Got another cherry last night. She wanted me to use a rubber but I told her I wouldn't - it's like taking a shower with a raincoat on - and she let me go ahead anyway." So I believed that crapola and it cost me some great sex, probably. Karla and I continued dating and just making out through most of our Senior year but she was getting sexually frustrated even more than me, I think now. But she didn't want to get pregnant in HS. Finally I took an advanced Biology course in our HS with an actual college level textbook with details on human reproduction and the female ovulation cycle. I let Karla borrow it and SHE devoured that section - and when she felt it was safe for her, let me have her one night.

This was just after her turning 18 and Karla really became more "open" herself. Maybe it was reading that biology textbook. One night she started rubbing my cock through my jeans and I unzipped myself - she grabbed my cock and it became a hand job. Just a few nights later I sort of discovered her clit and just kept rubbing that based on her responses. Her hips started jerking and she was moaning a little. Finally, she grabbed my hand with both of hers and forced it away. She either was scared to orgasm or had a small one already and was in that clit super sensitive zone. But on this next date I didn't know I was REALLY going to get lucky, but I guess I did. Again we were at a Drive-in movie in the big Buick. We were just making out and I had my fingers down her jeans and inside her panties and in her cunt - when right after it got totally dark she just pulled her jeans down and her panties off - and I wasted no time pulling my own jeans down as well.

Karla never really got very wet (at least with me the few I times I touched her there) - her pussy was always just kind of had an oily feel, slick and easy to get a finger in but kind of tight. I knew absolutely nothing about oral sex back then (other than French kissing and sucking tits) and Karla never mentioned it either - for her or me.

And now here she was with her pants down and her legs spread and pulling me on top of her with my 18 year old diamond cutter erection. She wasn't a virgin but boy was she tight (only years later did I get some glimmer of just why...) I was pushing and relaxing and pushing again and slowly making some headway - but the lack of plentiful natural lubrication AND the incredible rhythmic hard squeezing her vagina was doing around my cock meant that I soon started spurting when I was only halfway inside. Still it was the absolutely best feeling I had ever had in my life. I almost passed out. Sure beat masturbation!

But then I got a worried feeling that she MIGHT have gotten pregnant anyway - and that nervousness ended our sexual activity for that night - and forever more as it turned out. What were the chances my very first sex would be a girl with that mythical snapping twat? Well, obviously not mythical but still a pretty rare thing. I've never found another woman myself with that kind of ability - natural or purposefully developed. But I am not any kind of "stud" either - and in truth have only had sex with 7 different women my entire now 68 years of life.

I only had one other date with Karla. We had been together for almost a calendar year and most of our Senior HS year - and now our Senior year was almost over. We went out again a few days after our actual sex date - and she wouldn't let me touch her cunt - until right at the end when she grabbed my hand and stuck it between her jean covered legs for a second. She also told me her old boyfriend John had called and asked her out and she was going to start seeing him again because "you and me were never officially 'going steady' ". Yeah, right. Maybe John used rubbers, no problem. Maybe John lasted longer - a LOT longer. I missed untold encounters with that wonderful tight snapping twat because I was too stupid/proud to "wear a raincoat taking a shower". Uh, Dummy - it WASN'T taking a shower, ever! And a lubricated condom would have helped me get in her AND last longer. Idiot.

Anyway, I never called her again and spent about 2 days deeply, deeply depressed - but luckily youth is resilient and I had a pretty busy summer lined up anyway. Even before I met Lynn. Karla did call me a week or two later "just to talk and see how you are doing" but I just played it real cool and talked about nothing - no intimacy or really asking about her doings. And that was it. The whole rest of the year I hardly spoke to Karla - saxophones sat on the other side of the band room from the clarinets where I sat. Funny, but almost all our mutual friends we did things with dropped her and stayed friends with me. John and her broke up pretty quickly again, and John went back with his true "steady" a rather strange girl named Zoey (almost a narcoleptic actually - she fell asleep a LOT on bus trips and elsewhere - maybe from all the condom protected sex they had.) And Karla got a whispered rumored "reputation" for giving handjobs or even blowjobs on first dates - and would go with anyone who asked her out. She didn't go steady with anyone else I ever heard about. At the end of HS we signed each other's yearbooks - her words to me were something like "You are a great guy. I should have stayed with you." I heard a few years later she married a farmer in Illinois farming country soon after HS graduation. Wonder if she kept her wonderful strong athletic figure and "hidden talents" all these years? I don't have a clue.

I dated a few girls my senior year and even double dated Senior Prom with John and two girls who were like sisterly close to one another (not Zoey, strangely). I think both these girls were interested in John - but one had to go with me. (Kind of like those girls at the annual ball in "Harry Potter and the Goblet of Fire"). I drove that night and John and his girl spent a lot of time looking for each other's tonsils back there. My date would hardly talk to me. Oh well, John was just a normal "average" guy in looks - about 5'10" and 150 lbs. and a pretty good trumpet player and two good normal eyes. And girls liked him. a LOT.

One other interesting sexual thing happened with John, me, and another girl in the band - Carol - once our Senior year. She was a longtime friend of mine because her Dad and mine worked together as IBEW linemen for the local county electrical utility. We had all done something together that day and ended up in my Dad's old 1952 pickup truck this time taking her home. One bench seat and she was sitting between us. John must have just given off some male pheromones (and I know scientifically that's pure BS) because he and Carol were soon French kissing - but then she turned to me and did the same. We both tried to feel her up - but she kept my hands (at any rate) from feeling her tits - while she kept Frenching us both for a while. It was exciting but just didn't feel right. Carol was attractive, but not so much to me, normally. After this she kind of hinted I should ask her out - John was definitely back with Zoey - but I just did not want to. I just never was "stud" (meaningless just fun sex and.or conqueror of girls) kind of material.

I was a hopeless romantic in the "true love forever" and KISA - DiD mode. That's "Knight in Shining Armor (saves) Damsel in Distress", of course. I had grown up reading a lot, especially Science Fiction and Fantasy - and specifically Edgar Rice Burroughs and Robert A. Heinlein. Tarzan saved Jane - and loved her and only her (and vice-versa) for life. John Carter of Mars saved Princess Dejah Thoris and - ditto. And even Heinlein espoused this basic ethic and romantic morality in most of his "juvenile" SF - like "Starship Troopers". Of course, "Stranger in a Strange Land" and "The Moon is a Harsh Mistress" had some more liberal sexual memes.

Lynn started confiding in me about some of her own problems as an unplanned for "baby" daughter whose closest in age sibling was already 16 years old when she was born. Her mother and father were already in their late 50's when she was 17 and I came along. She told me her mother had been rather cruel to her at times - like tying her to her bed and/or locking her in her bedroom before she was school age.. As an older and (ahem) more experienced male I felt like her knight...after about a year of dating and only to "second base" and with me away most of the school year at the University of Illinois (where I was pretty much unhappy and on academic probation anyway) it was finally summer again and our dating intensified. Lynn was over 18 herself, now. Finally, one night at the Drive-in again and after the first feature movie's worth of heavy petting with our naked chests pressed together, I reached down once more to feel her pussy - and she let me! She was wearing a dress or skirt as she now almost always did on our dates - and I quickly removed her panties. I also pulled my own pants down and - darn it - my erection was gone, the victim of "blue balls" from the almost 2 hours it had ALREADY been hard and unfulfilled. I calmly just explained it to her and caressed her literally soaking wet pussy. Quite a difference from Karla's - no doubt about it.

Just a day or two later we tried it again - and her panties came right off much, much earlier that night and soon I was gently breaking her hymen. She bled quite a lot and I again, did not even get it all the way in (just for her consideration) while lasting much longer enjoying her incredible slipperiness and heat. About a week later we did it again all the way and she STILL bled a little more - but after that she was hooked on sex just as much as I was. I was still not using any condoms but I was trying to stick by the basic ovulation "rhythm" method - and that seemed to work all that summer. By the end of the summer she was undressing fully in the car as soon as it was dark and on the way TO the drive-in or our parking spots - letting me fondle her pussy while she grabbed my cock - though she didn't know about blowjobs yet - and I always wanted to just fuck her anyway. She had an incredible sex drive and it actually matched my own.

Just maybe a week after I finally took her virginity I was over visiting her at her parents house. They actually kind of liked me as just a kind of nerdy "harmless" older college kid and didn't worry about me, at all. Oops. They had a finished basement as a game/TV room and that's where Lynn and I spent a LOT of time making out. This time I soon had her panties off and I had her on the floor pumping my cock in her very wet pussy. She had her hand in her mouth and moving her head back in forth in ecstasy when her old man started down the steps - I sat quickly right back up on the couch and she grabbed her panties and ran into a half bathroom to fix herself. I don't see how he could have missed what was going on but he never said anything except "where's Lynn"?

"In the bathroom doing something" I replied. "OK" he said and started back upstairs. There was a wet spot on the rug where we had just been AND it smelled like sex, to me. But he either never noticed are really didn't care.

Well, summer ended and I had to go back to college - even though I was SO "in love" with Lynn and addicted to the sex with her. I didn't have a car and was restricted to very limited bus or train weekend trips back home. I was basically failing my core subjects and just wasting money. I had wanted to be a scientist or technologist of some kind and my declared major was "Engineering Physics" but all my initial college placement tests put me in almost remedial math and science courses - while I DID end up in an advanced English course - with a whole bunch of other really smart Freshmen. Our first day of class the Prof just started with calling out names of stuff I had never heard of - paintings and sculptures and obscure but "important" books - and every time several hands would shoot up with a short explanation of the significance and they really knew what it was. I was starting to feel a little inferior - then he said "Le Sacre du Printemps" and NO ONE ELSE raised their hand so mine shot up: "the Rite of Spring by Stravinski". Bingo, my love of classical music and an excellent in depth HS band history paid off. I ended up with a B+ in that class with C-'s and D's in "Advanced Algebra 101" and "Chemistry 101". Turns out my HS was a tad deficient in science and math while having an excellent English department. Who knew???

justbobkc
justbobkc
678 Followers
12