100 Women: A Life Story of Sex and Redemption

100 Women: A Life Story of Sex and

Redemption

By Tyler True

Copyright © 2015 by Tyler True All rights reserved. This book or any portion thereof may not be reproduced or used in any manner whatsoever without the express written permission of the publisher except for the use of brief quotations in a book review.

First Edition Published by Tyler True, 2015

Third Edition, August, 2020

10 9 8 7 6 5 4 3

Table of Contents

Introduction

1 - See Ya Later, Stupid Virginity

2 - First Load

3 - The White Titanic

4 & 5 - Ménage à Failure

6 - 72 Virgins? No Thanks

7 - The Town Dump

8 - The Artist

9 - The Cat's Ass

10 - Trainspotting

11 - My First Fight

12 - Blackout Sex

13 - Noodle

14 - Premature Ejaculation

Let the Adventure Begin

15 - Some Vaginas are Wont to Bleed

16 - The Russian Princess

17 - Dude'd

18 - His Tossed Salad

19 - Anal Virginity

20 - Balcony Sex

21 - Brown Shania Twain

22 - Meowser

23 - Giant Brittany Spears

24 - Fist

25 - High School Girls Are Easy

26 - Jay Leno

27 - Deck of Death

28 - Shovel Face

29 - Dirt Bag Filth Trap

30 - First Squirter

31 - Turd and the Cougar

32 - Brokeback Mountain Style

33 - Spicy Chili

34 - My Two Lies

35 - Her Tossed Salad

36 - James Bond

37 - Quebecois

Before the Military

38 - Aquarium Girl

Military: The Beginning

39 - IUD

French Training

40 - Gremlins 2

41 - Let the Sweating Begin

42 - I'm Going to Eat You

43 - Anal Prairie Bear

44 - One Sided Relationships

45 - Cry Baby

46 - Herman

Costa Rica

47 - Shitting Where You Eat

48 - Sober Pick Up

49 - San Isidro

Swiss Girls Are the Devil

50 - Fuck All Night

Mal-Pais

51 - Best New Year's Eve Ever

52 - General of the Air Force

53 - The Time Scale

54 - Anal Vixen

55 - MeMe

56 - Ingrown Hairs

57 - Bomb Face

58 - Stoney

59 - Hmmmm

Thailand

60 - Not a Hooker

61 - Is a Hooker

62 - Sweden

63 - One Sex on the Rocks, Please

64 - Invasion of France

65 - Vegas, Baby

66 - Anal Contract

67 - Anaconda Vagina

68 - Foot in Mouth Texting Disease

69 - AWOL

70 - Put it Wherever You Want

Central America Trip #2

71 - Skinny Mexican Saved My Life

72 - Cell Phone for Anal

Belize

Honduras

73 - The Jew of New York

74 - Monster

75 - Mongrel

76 - Dumb Dumb

77 - Puddles

78 - Fat Chicks Love Anal

79 - Astrology

80 - Mental Institutions Are Romantic

81 - Eskimo Anal

Southeast Asia Fucked Me Out

82 - The Ho

83 - Cancer Vag

Captain Hook

84 - My Pickup Tactic Works

85 - Czechoslovakian Angelina Jolie

Cambodia, Vietnam & Malaysia

86 - Chubby Princess of Persia

87 - The Ass of a Tennis Player

88 - Snuffleupagus

89 - Snug as a Bug in an Indian Rug

90 - Norse Demon

91 - Russian Concubine

92 - Russian Model

After S.E. Asia

93 - Down Under

After Mexico

94 - My Second Virginity

95 - Lepsy Daisy

96 - The Perv Scourge

Please, Be the Last Time

97 - Eat, Drink, Fuck

98 - India Jones

99 - Big Bird

100 - French Immersion

The Final Edition

Conclusion: My Redemption

Introduction : A Man-Whore's Beginning

The hardest part of writing this tell-all-tale was not sharing incredibly intimate details (I did that on a nightly drunken basis), it was making the list of women I had slept with. I made sure to lose count so that I couldn't tell any woman who asked how many I had been with. At the age of 22, I'd made a list (to satisfy my own curiosity) and it was already at 50. After that silly exercise, I had to somehow make myself lose count again. I did my best to not pay attention and after 15 or so more women, I had basically achieved my goal of being an ignorant slut.

When I started writing this memoir, in 2015, I actually figured that I was around 175, give or take 25. After spending weeks making a list, my number actually turned out to be 135. It goes to show that guys usually do unwittingly exaggerate in this regard. In the 5 years since I wrote that first edition, I've slept with 30 to 40 more women, which puts me at way too fucking many. Or, in other words, exactly what I originally thought I'd slept with – I was seeing into the future for this final edition, I guess.

I picked 100 of those women that either had interesting stories, meant something to me, whom I owe an apology to, or helped me get to where I am now – a man who no longer craves sex to fill a void.

If you are offended easily, or feel that anyone who partakes in casual sex should be burned at the stake, then maybe this book isn't for you...unless you enjoy feeling hatred. The only thing that I ask is if you find my words too vulgar, or graphic, that you skip to the conclusion and read about my plans for the future. The conclusion (my redemption) is really the entire purpose of this sex book. That being said, it will make a lot more sense if you read from beginning to end. Plus, this memoir is really only 60% about sex...maybe even 50%.

I originally wanted to write a screenplay to immortalize my spank bank. After not too much deliberation, I realized that this could only work in a book. The audience needs to understand what's going on in my slutty little brain to truly appreciate how a man-whore can change his ways. As any alcoholic war vet will tell you, "I've seen some things, man." I've really seen some things, man, some things that cannot be unseen. And my interactions with women WERE like a war: a constant battle to see who could get the upper hand in the relationship. To make them like me more than I liked them. To ultimately get more energy from them than they got from me. And where I thought I could win the war was in the bedroom.

I should start out with a brief introduction about myself so you can decide right off the bat whether you hate me or not. I was born to a runaway teenage mother with an 8th grade education, and a 35-year-old father on crutches for life – literal walking crutches.

My mother first ran away from home at the age of 10 because of things that I'm not completely aware of. I know that it was some kind of abuse from her step-father; whether it was verbal or physical is of no consequence at this point. She once mentioned it was because nobody could control her or tell her what to do – I can certainly relate to that. She was caught after about a year, but escaped again at the age of 14. This time she was much better prepared and never looked back.

My father was at the disadvantage of being labeled a genius; a disadvantage that brings all sorts of expectations and pressure. Fortunately, for him, he was hit by a drunk driver while riding his motorcycle, at the age of 18, right before heading off to university. All expectations and pressure crashed down onto the asphalt, along with his destroyed hip. He was now just a simple cripple able to give up on life and live off of government assistance – he always referred to himself as a cripple, so I'll use that word as well. It also gives you a warning as to my ambivalence towards political correctness. My dad spent many years in the hospital, during which that facility so graciously gave him a staphylococcus infection, that he lived with for the rest of his life.

He has always liked to brag about the fact that doctors continually told him that he should be dead. Unfortunately, for his unhappy existence, he was too smart to just go away and die, and kept himself alive with healthy foods and copious amounts of marijuana. He was apparently quite a musician (I've never heard him play) and can fix anything; alas, his bitterness at the world kept him from ever finding a job or doing anything with his life. A bitterness which could be accounted for, if you believe in living that sort of way, because the world dealt him a shit hand.

Bitterness excuse #1: a plucky little lawyer found my dad in the hospital, right after the accident, and got him an amazing settlement of $30,000. Now, this was 50 years ago, but even with inflation times a hundred, I would think that $30,000 was probably not enough for a man that would never be able to walk again. He later found out that his lawyer worked for the insurance company of the man that hit him – good ol' insurance companies, always there for the little guy.

Bitterness excuse #2: the hospital messed up multiple operations and gave him a staphylococcal infection, adding to a stew of hate for any doctor, and essentially the world, that would keep him locked up in his own world of misery. Now, I could say that my mother added to his bitterness and desire to do nothing by leaving him. But he was already living with his disability for 16 years before ever meeting my mother, and had never had a job at that point either.

My mother met my father by renting a room in his house. She says he protected her from one of his creepy friends one night and she started liking him. It must have been instant love because my mother had my older brother shortly after meeting him, at the age of 17. Then, a year and a half later, she popped out this miraculous little angel that is so generously donating his sex life to the world...maybe even his actual life.

Fortunately, for me, their true love ended after 9 months of my life. My mother left my father, and the beautiful west coast of Vancouver, British Columbia, to live in the prairies of Saskatchewan. I'm sure almost everyone outside of Canada has never been to this province (nor most Canadians), and I can pretty much say with 100% certainty that, unless you're going there to work, you never should! I've been to quite a few places in this world and not one of them has ever come close to the shittiness of the Canadian prairies. I can't argue with her decision to leave beautiful British Columbia, and my father along with it; because if she had stayed with him, then I'm quite sure that at this moment I would either be a felon or a corpse.

After this move, for which my father became even more bitter at life, my mother proceeded to do something that very few teenage, high school drop out, single mothers ever do – she became a success story. She moved to the prairies for two reasons: She had family there – the family she had originally run away from, minus the step-father. And the provincial government of Saskatchewan has some very generous legislation in regards to helping single mothers become trained in a trade of their choice. Saskatchewan pretty much has to help drop out, single, teenage mothers because that's basically half the population of that giant, disgusting, garbage heap...shit, sorry, Sasky. You helped my mother, and ultimately me, so I'll give you this round...but that's all you'll ever get from me you filthy, ass hole of the planet...shit, sorry. There might still be some traumatic emotional injuries from that experience.

Upon arriving to the prairies, my mother got her general equivalency diploma and then went to school to become a dental assistant; all the while raising two toddlers and working in I don't know how many jobs. This is basically what you have to do to succeed as a single parent – give up everything resembling a life, in order to give your kids what they need. Unfortunately, that is not something a lot of single, high school drop out mothers ever do. Not with an amazing welfare system that gives them the opportunity to do nothing but watch trash all day and eat mac 'n' cheese.

Eternally grateful sounds like a spit in the face in regards to my feelings toward my mother and what she sacrificed for us. I would make up my own word to truly demonstrate my gratitude, but it wouldn't mean anything to anybody, so I'll just stick with that lackluster verbiage.

A dental assistant does not make good money, by any stretch of the imagination, but it's better than minimum wage. So, along with the other one or two jobs that she always worked, usually as a bartender or waitress, she was pretty much able to give me and my brother what we needed. I couldn't play league hockey, the national pastime of Canada, nor could I do any extra-curricular activities that required a driver or any commitment of time from an adult, but we had what we needed.

Also, since she was gone pretty much all of the time, it gave my brother and I the opportunity to raise ourselves – I highly recommend this to every child. I would see my friends being pampered by their mothers (doing their laundry, cleaning the house, cooking dinner) and even at a young age I was proud at being able to take care of myself. I was independent and as long as I got straight As, which I always did with very little effort (thanks for the genetics, dad), then I was able to pretty much do whatever the hell I wanted.

Most parents (including my mother) would probably have angina to learn of the things that I did with all of that freedom: smoking cigarettes in grade four, drinking and smoking pot consistently by grade seven, stealing, vandalism, hanging out with thugs that stabbed people, and overall just doing a lot of terrible things. But I argue that one needs to go from one extreme to get to the other. I guess some people are just born with the ability to be good, responsible citizens (my brother being the prime example, as he has never broken a rule in his life), but I was not born with that lame trait. I've had to learn all of my morals the hard way. The great thing about learning things the hard way is that they are stuck with you no matter what. I'm convinced that the guy who has never broken a rule is going to snap at some point, and go on a rampage that makes my behaviors seem like amateur hour. I'm waiting for it, Brother.

My mother always had a guy around. She was a very beautiful woman and men were always after her – I hope you can appreciate the joy that my teenage friends had in this regard. There were a few guys that were around for many years each. You could say that I've had three different step-dads, which, unfortunately for this book, I don't have anything significant to report on that front. They were all decent guys that helped me out and taught me lots of things. From a Psychological standpoint, you could say that my man-whorish behaviors may stem from my inability to attach to anything due to my chaotic early life of periodic abandonment; but to that I say, "Thank God! I believe anyone with an ambivalence to attachment will say the same thing, I'm happy to be this way."

Please tell me how it's healthier to depend on others for your happiness. I derive a lot of my energy and happiness internally. It's not a fear of attachment because of a subconscious thought that people are going to abandon me, I just don't crave it in any way. I never think someone is going to leave me – enough people enjoy my company, and if they don't, then I'm okay with that. I like to experience people while they're in my life. But when the time comes to say goodbye, I am more than capable of saying, "See ya later," and moving onto the next chapter in my life. Getting stuck in relationships because you're afraid of losing people, or afraid of being alone, is a far worse crutch than being an independent loner. Of course, that's just my opinion, as this memoir is full of – please keep that in mind. On the other hand, you could also say that perhaps I was always searching for women to love me because of an absent mother – I'll let you form your own conclusions regarding that theory.

My mother worked her ass off and went back to school, when I was 13, to become a dental hygienist. Those glorified mouth janitors make pretty decent money, and my life got considerably better from that point on. She moved us back out to the west coast of Canada – Vancouver Island, to be precise – and I was in absolute heaven. It honestly never bothered me to go to another school (I went to seven different schools from kindergarten to grade 12). Even though I moved out there in grade 10 (my poor brother was in grade 12), and I was a loner for an entire year, I was still in heaven.

Vancouver Island will always be the most beautiful place on the planet to me. It's got everything a people hater could want: tons of wilderness without a soul in sight, ocean everywhere you look, wildlife walking on the streets, and a lot of people with a lot of money who are not just looking to kill you for fun. It was everything that shitty Saskatchewan wasn't and I was so happy to leave my best friends and move there – there's that ambivalence to attachment rearing its gorgeous little head.

I was basically a shy loner with braces in grade 10. But in grade 11, my mother and her husband bought me a rusted out, little white truck for my 16th birthday. Actually, I got the truck when I was fifteen and a half, which was probably not smart on their behalf since I drove it around without a license, and of course without them knowing. I rarely ever got caught doing any of the bad things that I was addicted to doing. I was still getting straight As at that point; actually, in grade 11 I won the academic award, which was quite amusing to me and my friends that partied every weekend. I found it even more amusing since I was the only one who knew how little time I actually spent on my school work. The funny thing about our education system is, it doesn't measure actual intelligence, it measures memory, and mine is pretty darn good. Nonetheless, you can see why I had the sorts of freedoms that I did.

That truck kick-started my life of adventure by giving me absolute freedom, and it also got me friends. Friends that used me and that I used right back. At its core, that's basically what every relationship comes down to, isn't it? My life started once I got a vehicle. My dear mother even gave me a gas card, so I could pretty much just drive around listening to music until all hours of the night. It was amazing and I can't be the only one whose life changed drastically after getting their first vehicle.

I was a natural driver, as my bad friends and I had been stealing family member's cars since the age of 13. By the time I was 16, I was already very comfortable behind the wheel. Me and that truck shared more beers than you could imagine. Oh right, I know a lot of people, if any people even read this, will freak out about this, but I drank and drove a lot. I mean A LOT. In my life, I've probably been over the limit and driven a thousand times. It's just what I did.

I never hurt anyone. In fact, besides getting eight 24-hour suspensions for blowing warnings on a breathalyzer, I never really did anything wrong. You will say that drinking and driving is wrong in itself, but to that I say, "Don't you actually have to be showing that you are impaired before you are actually committing a driving crime?" It was pretty tough for me to lose control of my senses when drinking. I don't do that anymore, so relax.

Luckily, for my life of adventure, I made my own laws in pretty much every aspect of life. I said to the cops, "Let the games begin." It was their job to catch me and my job to not physically hurt another human being. That is the only law that I abide by. If I do not negatively affect another living creature, hurt the environment, or cost anybody any money, then in my opinion the government has no business ever bothering me. Remember me saying I have a sparkling sense of morality? Well, you'll probably disagree with that upon hearing this rant on the law; but I am still this way even after going through my transformation.

So, now that you probably think that I'm a disgusting, law breaking danger to society, it's time to get this fuck show rolling! I'm going to tell you how I have become the person I am today and how I think we're going to turn this troubled world around. Yeah, I'm a crazy person, big deal. This is also kind of like the eighth and ninth steps in the Alcoholic's Anonymous 12-step program to recovery, except this is for sex addiction.

I'm essentially making a list of all of the women I've harmed and trying to make amends; although, a lot of them probably won't see it that way. It's supposed to be entertaining and make you laugh as well – you can't do that without offending some people. There is a great deal more to this than sex stories and humor, though, as you'll see if you don't skip through.

Let the fuckfest to redemption begin.

1 - See Ya Later, Stupid Virginity

Any memoir about a person's sex life has to start with how they lost their virginity, doesn't it? I pretty much wanted to lose my virginity at the age of 11, but was never able to find a willing combatant; probably because of my terrible, terrible teeth. My mother – thank you, mother (she's not allowed to read this so I don't know who I'm thanking) – gave me her congenital syphilis ridden genes and probably felt guilty. So, she got me braces at the age of 13. Those stayed on for the next four years and pretty much ruined any chance at losing my virginity. At the age of sixteen and a half, those metal bastards came off and my career began.

I was chomping at the zip – zipper that is – to get good at this sex thing, so that I could really impress a girl whom I actually cared about. I could seriously not have cared less about the girl that was going to take that stupid thing off my hands; pardon the pun, but that thing was in my hands pretty much six or seven times a day.

Along came Number 1. She was kind of a notorious character among our cohort because of what happened between us. I can't imagine why, but I actually made quite a few girls go a little insane and do some not very nice things to me.

Number 1 had a big ass. I love asses. I am an ass man through and through. Actually, it's the whole hip and ass combo. She's gotta have the curves because just a nice ass with straight hips won't do anything for me – might as well just sodomize a 12-year-old boy, no? You can keep your breasts and face, and whatever else guys care about (I won't say legs because I'm pretty fond of those too). If you give me a nice ass with big ol' hips, then I won't be able to focus on anything else in the room. So, Number 1 had a big ass and wide hips, which I thought I loved. Turned out it was a bit much for me – could have just been her personality that turned me off, though.

I knew Number 1 from high school and I used to always think that she was really cute – man did I want to bend that ass over. I'm not sure how she got my number, but she was calling me all of a sudden in the summer going into grade 12, and we started hanging out a bit. I have no illusions that everything that has happened to me from this point on was all my fault, and the consequences of how I treated women has been haunting me my entire life.

Here's the thing, I treated women quite well. They loved being around me and thought that I was super into them. I caressed their hair, I loved to cuddle, and I pet them gently all over their bodies. Truth is, I was quite affectionate when I shouldn't have been. I cared nothing for most of those women, yet I was making them think that I did. I didn't realize it at the time, but now I know that what I was doing was probably the worst thing you can do to a woman. It was worse than cheating, it was worse than lying, it was worse than beating them – making them fall in love and then nonchalantly throwing them to the curb. I have no idea how many women I led on, but it was far too many.

I made Number 1 think that I was way more into her than I actually was. You see, I had this void inside of me (I think most people have one) that I used to fill with women. I didn't just want to have sex with them, though, I wanted them to really love me before I could move on. I'll be paying for that sort of karma for the rest of my life, and deservedly so.

After a few days of hanging out with Number 1, she decided that I should lose my virginity on my 17th birthday, which was right around the corner. The sex came and went just like the first day at any new job – it was awkward and I just wanted it to be over so I could get better in the following days to cum. I didn't blow my load and I didn't really enjoy it at all. I hear about these guys that climax within five seconds on their first time, and the multiple times after that, but not me. It could have been because I had zero feelings for her, and even really started disliking her after not too long. But more than likely it was simply because I didn't know what turned me on yet.

I had boring old sex with her three times (including one time on my driveway, during a party had by my parents), never once climaxing, and, mercifully, the 'relationship' ended. You want to know how it ended? I sure hope so. I drove her home one night and she told me that she wanted more from me. She wanted us to be legit boyfriend and girlfriend, to which I said, "No thank you." To which she said, "Then I want to break this off." To which I said, "Amen, hallelujah, baby Jesus!" Only in my head, of course – as the baby doesn't like his name being used in vain, apparently.

She got out of the truck and it was my first, of many, happy breakup aftermaths. I honestly can't think of anything else in my life that made me happier on such a consistent basis than when one of my 'relationships' ended – the sweet ecstasy of freedom once again.

The next day, Number 1 called me. This was before cell phones, mind you, so I was sitting on my stupid house phone and she started chatting to me like nothing had happened. I was being quite a jerk because I mistakenly thought the whole thing had ended, and that was that. She wanted to take back what she had said and just hang out like we were before, to which I said, "No thank you." Actually, I may not have been so polite. In fact, it may be possible that I see a lot of my past with rose colored glasses.

She asked me why I was being such a jerk, since before this I was grade-A boyfriend material. I responded with, "We're not fucking anymore, so I don't have to be nice to you."

Oh teenage Tyler, you stupid, stupid child-whore. This was truly my first experience with the saying, "Hell hath no fury like a woman scorned." In all of the reading I've done, and I've done a lot being the curious loner that I am, I'm yet to find a more concise cliché in the English language than that one.

After her yelling at me for some time about being such a jerk (her favorite word), I managed to get off the phone. I figured that would be that and she would move on to the next guy that would add to her emotional baggage, that is sure to weigh down every woman by the age of 25. Alas, karma does not work so neatly...or maybe it does. A little time went by and I received a phone call from a school acquaintance. He told me that Number 1 and another girl (whom I was also not very nice to, but in a completely different way of incessant teasing at school) had broken into my house and done various things to my personal effects. Those girls had stolen my retainer, as any person in the aftermath of braces will tell you is very necessary, and they had put ex-lax in a bunch of food in my fridge.

Now, the retainer, okay, I could respect that, but to endanger the health of my poor mother was a war crime. I thanked that young man for his tattle-tale ways and then asked how the heck they had gotten into my house. Apparently, Number 1 was used to getting even with boys, as she had recently been dumped, and she was planning in advance on how to get me if I fucked her over. So, one day when I so trustingly pushed the code on my garage door key pad, she watched. She watched like a young lady who knew she was going to need to sneak into my house to exact revenge, for what she didn't quite yet know, but was sure to happen. She remembered. She remembered that code for many weeks afterward. Sly little lady...well, not so little, but quite sly.

There was not much to be done about the whole thing as they had my precious retainer as hostage. So, I called them with threats that I had already phoned the police, to which they panicked and drove my retainer straight over. Now, of course I wasn't calling any stinking police. I was no fan of the cops and was, probably always will be, at war with them; simply because they don't agree with lots of the laws they enforce, yet they still enforce them. I have no respect for people who live in black and white. They know corrupt politicians controlled by money make legislation for their own greedy purposes, yet they still enforce these outdated laws. Plus, the police would have just laughed anyway. Those girls didn't know that, though – they returned my retainer and apologized profusely. Sorry, ladies, not enough.

Grade 12 started and that poor girl that I used to incessantly tease got it much worse...poor thing. To be fair to myself, she secretly loved the teasing and she did things that made my mouth act on its own accord. She would say things like, "Bless me, after sneezing. She would also make daily statements, in her high pitched voice, about things that her mother told her concerning life, which always started with an opening line of, My mom says." Let ye who would be able to ignore such things cast the first stone.

Number 1? Well, she had something else in store. Halloween was just around the corner and I had the bright idea to shove a pillow around my ass and cum dressed up as her. Everyone in the school knew exactly who I was because as I said before, she had an anatomically dis-proportioned ass (maybe I didn't use those words, but she did have one), and it was quite obvious who I was making fun of. It was quite obvious to the teachers as well, who made me take the costume out of my pants and go back to being just skinny ass Tyler.

I figured that was revenge enough and I was done with this girl; unfortunately, she was not done with me. For the next 10 years, until she got married, all I heard from her friends was how she never shut up about me. This may have been slightly my fault because I kept sleeping with her over the next many years. Don't judge me! Sex addiction holds no grudges. I didn't even enjoy it and rarely ever climaxed. She was always just there by my side if I was at the bar, and she would never take no for an answer. In fact, she once negotiated with me that if I allowed her to spend the night at my house, then she would let me take her anal virginity.

I'm not going to get into my anal fixation just yet, but I've already told you how I love asses – anal sex kind of naturally follows, doesn't it? Anyway, yeah, it may have been slightly my fault that she was a little preoccupied with me for way longer than it ever should have lasted. I should have just told her to leave me alone and been steadfast when she ignored my pleas.

I'm sorry for not being more direct with you, Number 1. I'm also sorry that I made you think that I liked you more than I did, and for being a big jerk. An apology I will be making many times over. I hope you're happy in your marriage.

2 - First Load

Ahhh, Number 2, the first girl I actually blew my load with. And let me tell you, IT WAS A LOAD! She told me it leaked out of her for many, many hours afterward.

Number 2 was a chesty little Asian girl that was one of my first friends in high school, after moving to Vancouver Island. She was a very friendly and boisterous person with giant, beautiful breasts. As I've mentioned before, I'm not much of a tit guy, but there was always something in my dumb man-brain that would sometimes set me off when I saw a beautiful pair of breasts.

It wasn't long after the Number 1 fiasco that a friend was driving me and Number 2 in his car. We were taking her home, but before we got there she called my name from the back seat – to which I obviously looked – she then flashed me those big beautiful breasts and started laughing. Let me tell you, my dick moved instantly and there was no stopping what happened next. I told her I was cumming into her parents house with her so we could sin, and she said okay.

We went at it for hours, never once kissing. She was already quite experienced from a long-term boyfriend that she had just broken up with, and she really showed me the ropes. It was much different than the boring sex I had with Number 1. We did all sorts of different positions, and overall just had an amazing time. Oh hello, sex addiction, how nice of you to finally show up.

After a couple of hours, I finally put her in the position which, to this day, is my go-to for cumming – froggy style. Some may call it other names but I call it froggy. It's when the girl lays flat on her stomach while the man lays on top and takes her from behind. Oh my, what a position. A rampant ass man such as myself gets to push against that majestic softness, combined with the view that I like, and the ability to reach around to the clitoris (which I didn't know much about at that stage). I should tell you that I'm a fairly tall guy at 6'2", so I can usually rest my head above the girl's shoulder to take my weight, and use both hands to manipulate whatever I please. I was 17 at this point, so I wasn't doing anything quite that advanced.

I just laid right on top of her so that she couldn't breathe, and pumped and pumped and pumped. After about 30 minutes of that, and a surprising orgasm from her (which I had no idea about until she told me some years later), I blew my load. Oh my God did I blow my load – she was on the pill so I came inside of her, which I wouldn't have done in my older years. I kind of consider this my first time having sex – I was fucking hooked!

I never had sex with Number 2 again. That's a bit shocking because I am a true environmentalist that recycles everything, especially ass holes and vaginas. I think she got back with her boyfriend or something. Or maybe it was a bit awkward because we were friends and there was certainly not going to be any sort of relationship forming from that encounter; I'm not sure if I was her type, but she wasn't mine. I never would have thought to have even had sex with her if she hadn't flashed me those beautiful breasts. Either way, I don't owe Number 2 an apology, but I do owe her a thank you for being such an unbelievable lay. Maybe she owes me an apology for getting me addicted to sex! Although, I'm pretty certain that was bound to happen sooner or later. I hope you're happy in life, Number 2.

3 - The White Titanic

Number 3 happened shortly after Number 2. She was actually quite an attractive blonde. The first time I saw her I thought, 'holy shit, she's hot.' Then, she opened her mouth and that was the end of it. She was just so jittery and always letting loose a nervous little laugh after everything she said, which was usually not very interesting in the first place.

I was quite blond back then, and let me tell you, any ditsy blonde that gave us a bad name (making fun of blondes was quite rampant in those days of the mid '90s), with their stereotypical stupidity, did not get the General (my dick) out of bed for any battle planning. But this girl really, really liked me and who was I to say no? I still needed lots of practice in order to truly impress Ms. Right, who was sure to be just around the corner.

So, me, Blondie, and some friends went out camping. This was in grade 12, mind you, but in this area that I lived there were hundreds of empty campsites that you didn't have to pay for, and nobody patrolled; what an absolute paradise. We would often go to some beautiful lake to camp and party, and nobody ever bothered us.

Blondie was the reason my little white truck got the name, 'The White Titanic.' It was 1997 and 'The Titanic' was making big waves in the box office...don't judge me on my tragic puns. I was having terrible – at least on my part – no-penile stimulation sex with Blondie, while unbeknownst to me, my horny little friends were trying to watch through the fogged-up windows of my canopy.

Apparently, right when they got close to the window to try and peek in, Number 3 slammed her hand against the glass and squeaked it all the way down – just like Kate Winslett in the movie. Well, those buggers got a real kick out of that, but me and Blonde Einstein had no idea what had happened until the next day. The White Titanic was born and let me tell you, he was a fucking legend!

That truck was the ultimate party machine. I would load up the back of that thing with people and we would drive around doing whatever the hell we wanted. That is, until I used to get people to throw their empties in the back at every party we attended – no more room for hitchhikers after that. I'm starting to realize why the cops would pull me over for no reason.

The Principal of my high school came out one day to congratulate me on the fine collection of empty beer cans and bottles, that amassed to hundreds of dollars in refunds. Again, if you can get straight As with minimal effort, then I highly recommend it; nobody ever gives a shit what you do, as long as you're one of the top students in school...I guess that may not hold true for Asian parents.

Alas, like all of the most intense relationships that I've seen on TV, this one also had to end when I went away to university. He was already starting to sink on me when I had to get rid of him, though. The White Titanic was actually a giant piece of shit, but man, I loved him. On my final night with Whitey, me and a friend launched him over many a curb in a parking lot at three in the morning, as ol' Whitey was going to the auto wrecker the next day. Pretty much a metaphor of how I treated my relationships with women, I suppose. Boy, I sure loved that truck; rest in peace, White Titanic.

Since I barely talked about Number 3, that should tell you enough. It was terrible sex, I could barely feel anything (something that me and my skinny penis were afflicted with fairly often), and I pretty much never talked to her again. I was definitely not nice in the way I ignored her when I knew full well how much she liked me.

I'm sorry for being an asshole to you, Number 3, and for not taking your feelings into consideration. Also, I should apologize to any girls in advance that I will be making fun of in this book. Just keep in mind that nobody will get made fun of more than me. Sharing is caring.

4 & 5 - Ménage à Failure

That brings us to Number 4 and 5 – yes, they go together! There were only two high schools in my town, which led to some pretty interesting parties. I wouldn't necessarily say that there was some cliché feud between the two schools, as most people on Vancouver Island are pretty content – so lack that sort of pettiness – but we were definitely quite different. My school was considered the rich, snobby school, and the other was considered more of the free spirited, grungy school. Anyway, there were these two girls from that other school that I knew, and they were most definitely free spirits, which has always attracted me.

Me and my friends used to hang out in the parking lot of this church quite often. We were getting drunk on the holy spirit of whiskey and speaking in tongues. There was one special evening when 4 & 5 pulled up in their truck and told me to get in. I happily obliged and took them back to my house, where my mother and her husband had just bought a hot tub. Those girls pulled out a bottle of vodka and they started getting drunk.

I often smoked when I drank, and this night I was smoking in the hot tub. I made those girls a wager that I could smoke the entire cigarette without dropping any ash. If I did it, then they had to do whatever I said. I don't know where it came from, since I had never heard of anyone doing it, but it popped into my head, and I thank the god of sex that it did. They agreed, perhaps thinking it couldn't be done (perhaps wanting to do whatever I said), and I proceeded to tilt my head back and smoke the entire cigarette without moving. I succeeded, tossed that butt away and told them to do the first lame thing that every 17-year-old boy wants to see – girls kiss.

God bless their vaginas, those two best friends started making out in my hot tub, and I sat there with a big shit-eating grin on my face, thinking, 'holy shit, I'm going to have a threesome! Holy shit, I'm only 17, I'm going to have a hundred threesomes!' Unfortunately, if you're reading this literary spank bank thinking it's going to be filled with a bunch of group sex, then you better soak this one up, because it's the only one.

They kissed for a while, then waded over to me and said, "Don't you want to be a part of this?" My memory is a little fuzzy as this a long time ago, but I'm pretty sure that I had only slept with three girls before that evening – I still didn't know anything about sex. It's not like these days where a kid can go on the internet and learn about anything on the planet. Internet was barely starting to become useful in 1997, and nobody but the computer nerds were really using it.

Either way, I was clueless. I went back and forth, kissing them, and then we all got naked – the standard stuff. We moved into the house and into my room, which was only about 10 feet away from my sleeping parents' room. We then proceeded to have an awkward teenage threesome.

I told one of them to lick the other's vagina while I entered her from behind, which they quickly shut down without a care in the world for my desires. After that, I was lost. That was how I thought threesomes went down. Oh, teenage Tyler, why was my only threesome wasted on you? So, after they shot my fantasy down, I tried to stick my dick into each one, as the other lay beside us watching. I don't know if the hot tub made these girls dry, if they were as nervous and awkward as me, or if I just wasn't good at foreplay, but neither of them got wet – I was unable to really get any good penetration going. Oh, stupid teenage Tyler, I understand you not keeping lube around in your little, teenage nightstand, but why oh why didn't you know about the glorious properties of saliva? I stuck my dick into each of them and tried to get them wet, but it just never worked. I got a few inches into each vagina and nothing else would happen, as I couldn't move.

Number 4 wasn't comfortable with Number 5 just laying there and watching. So, she took me into the hallway and I lifted her up, while trying to insert my penis into her ridiculously tight vagina, against the hallway wall – parents sleeping on the other side.

Number 5 came out right as I was fully inside and asked what we were doing? Pretty awkward situation just writing about it, try being there. We went back into the room and fooled around for a bit more, as I unsuccessfully tried to get them wet. Alas, my only threesome ended quite tragically with no load being spent on anyone, and barely any penetration happening at that. Still, it's a story I like to tell to anyone who will listen.

I never had sex with Number 4 again, but I had unsatisfying sex with Number 5 multiple times after that night. I don't owe 4 an apology, but I kind of owe Number 5 one for also sleeping with her sister. More on that in a bit. Either way, I want you both to know that I appreciate the story.

6 - 72 Virgins? No Thanks

I will spend substantial time telling stories about women that I either had no connection to whatsoever, or had a connection to over a short period of time. There are, however, quite a few women who have had a very lasting impact on my life – girls that I would do anything for if they ever asked me to. Most of these women knew me for me and I was very comfortable around them. The sex wasn't all that good with some of them, but they were, and are, all very important to me.

I'm not going to say that Number 6 was really that important in my life, or that she has had a strong lasting impression on me. She's important because she was my first real girlfriend and the only person whose virginity I ever took (vagina, that is).

I was 18 years old and doing my first year of college when Number 6 was still in grade 12. I had known her from when I was in high school, and I really liked her then as well. It was all about that round ass. She was also quite funny and I was attracted to her personality as well as her body. I'm not sure how it all started happening, but I commenced in courting her.

I knew she was a virgin and, if I'm going to be completely honest with myself, at 18 years old, I was aware that my window for taking a girl's virginity was slowly closing shut. Yeah, in case you haven't already figured it out, I was a disgusting animal. Or, maybe it's not that disgusting to want to take a person's virginity. I imagine most of you out there have desired that; since somebody had to take yours, it only seems natural to want someone else's. But, unless you're some sadistic piece of shit who cares nothing for a woman's pleasure, then you probably lose interest with virgins after you've had one or two.

Anyway, she worked at McDonald's while going to high school, and one day I decided to buy her a teddy bear and some chocolates. I delivered my gifts to her workplace, in front of all those other young ladies, and started the courting process off with a bang. She had a big smile on her face and hugged that teddy bear close to her chest. I was, and essentially still am, a pretty big coward in terms of going after women. In that case, I shut my brain up and just did it because I really wanted her...or that ass...is there a difference?

Number 6 agreed to go out with me, and that started the three month process of trying to get into her virgin vagina. She had told me that an ex-boyfriend had made her do a lot of things that she wasn't comfortable with. So, she had a lot of negative connotations about boys, and sex in general – her baggage had started early...great. It took a while to gain her trust, and, of course, I let her down.

The first time we had sex was in a bedroom that was right beside my mother's bedroom (different house than the last story), and we had to be quiet. The first time I had her naked I saw that she had long blonde hairs around her nipples. I used to have a real thing about hair on girl's arms, on their asses, and, after this incident, on their nipples. It really turned me off right from the get-go. I told her that she had hair on her nipples and she told me that I did too. I didn't think that was a fair comparison.

Not only was that a turnoff, but it also became apparent that we may have been a bit too similar in our sarcastic and biting remarks. At that point in time, I guess you could say that I was a bit of a cocky asshole, and liked to make fun of people.

I'd like to think that behavior slowly went away as my confidence changed from a superficial bravado to an inner belief in myself. Unfortunately, at that time, as many 18-year-olds are prone to do, I liked to make fun of people and call them out for stupid shit they said or did. She was the same way and really had quite the acid tongue that she would burn you with at the drop of a misplaced syllable. It started becoming a situation where we didn't even talk to each other because it would just be something negative and snarky from the other person. Let's get back to the first time having sex.

I expected a virgin to have a really tight vagina, but she didn't. It was quite average and it was then that I realized that all vaginas are not created equal; some are just bigger or smaller right from birth. That was a pretty disappointing realization for me. I had figured that all those other vaginas I'd had to that point were bigger than my penis because of the cocks that had been in them before. Sadly, after much personal experience, I later found out that I am in a category where only 10% of vaginas fit tightly around my dick. Regardless, I didn't cum, and neither did she.

It was awkward sex because even though I had probably done it about six or seven times at that point, I was by no means a veteran, and didn't take the reins very confidently. I didn't end up having an orgasm any of the three times we had sex – six months and three times having sex. It was not a very satisfying relationship for either of us, so it just petered out and died. She actually became quite bitter at me for being such a disappointing boyfriend to lose her virginity to, with good reason. So, even though she didn't play an important part in my life, she's dear to me. Like any vampire will tell you, the first human they suck the life out of will always hold a special place in their black hearts.

I'm sorry for being a shitty boyfriend and shitty lay, Number 6. I was just a kid and had no idea how to make a girl fall properly in love with me, so I could truly break her heart. Perhaps it was a godsend for you that you didn't meet me later, when my dark skills were more highly attuned. I