While analyzing my list of girls I’ve hooked up with, it’s clear to me that I went through a serious slump after the debacle that happened with numbers 8 and 9.  I don’t know if I had some kind of mental block or what, but I’m pretty sure that that experience set me back a few months in my learning curve.  My social circle was pretty much destroyed, and with that went my sources of  sex.

You see, as I was first learning pickup, pretty much all the hookups I got were through some kind of social circle, or just being in the right place at the right time.  I had no game.  Straight up, I couldn’t seduce a lamp-post.  I was just getting more accustomed to putting myself out there into the arena, and when you go out partying all the time, you’re literally bound to run into someone who will bang out.  Just by sheer luck really.

So for the next couple months, I was working on a couple different girls but I kept encountering this issue where I was deathly afraid to escalate.  I still kick myself for this when reading this list, because I missed out on a MAJOR hottie that was really into me that I met in one of my classes.. but due to chodeliness and lack of balls, I waited way way too long to make a move on her.  I got dropped into the friend zone, and when I finally got the balls to make a move, my window of acceptable sexual escalation was long closed and I got rejected.  Hard.  It was awkward.

So I learned my lesson.  You have to close.  You have to escalate. HAVE TO.  There is no seduction without physical escalation, and you have to constantly be moving forward.

But it really took me a good few months if not over a year to get that issue handled.. Resulting in mostly sexless life and frustration.  And sometimes, going after girls that were way beneath my standards due to sheer frustration with the fact that I could not get laid.  My self-esteem was taking a beating as I was trying to meet these new women and just getting rejected quite a bit.  It sucked.

Basically, I barely remember what happened with #10.  All I know is that it was the summer between my sophomore and junior year, and I was hanging out with some kids I knew from high school, and one of them was this nice girl who was cool to hang out with, but she was really unfortunate looking.  A little overweight, wore way too much makeup, naturally unattractive face… etc.

Bottom line, I was drunk off my ass and banged her in a car, or something.  I honestly don’t remember because after I realized what I had done, I didn’t want to think about fucking her ever again, so I’ve pretty much blocked this out of my memory.  It definitely happened, but I do not know the details.

Chalk this one up to a stupid, drunk fuck.

This is actually my first experience with banging a chick I was totally not attracted to, though there will be a few more of these stories to come.. especially the next few girls I banged while I was getting out of my slump. Basically I had almost an entire year of banging infrequently and low quality girls before I started to get to the next level in my game.  And that’s when shit got awesome.

So, double-digits.  In the least glorious fashion!

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Basically, this girl was totally nuts.  She wasn’t the most attractive girl, I’d say she was about 10-15 lbs overweight, but she was only like 18 so it wasn’t really that bad.  Her face was nothing special either.  But what I really enjoyed about this girl is that she was just fucking hilarious.  Like every time she would walk into a room everybody would kind of turn to her because she was constantly the center of attention.  It may be hard to describe this type of person, but she exists and everybody was pretty entertained by her.

So anyway, I love these types of people who can really work a room, and she was one of them.  It made me want to fuck her mercilessly, despite the fact that she was like a straight up 6 on the rating scale.

So we’d all go out as friends and get blackout drunk and then end up hooking up or something, and one night I just kind of woke up in her bed and it was pretty funny.  But to be completely honest I kind of liked this girl.  Which is weird to say, because now my standards are definitely higher and I’d never really be attracted to a 6 like that.  But back then I had a little less confidence in myself so I was happy to be occasionally gettin it.

What sucked was that she was totally nuts, so every time she’d get drunk she’d act all into me, but then in the morning she’d pretend like she didn’t like me any more and make these retarded jokes about how she hated waking up when I was there.  Which is perfectly justifiable, I should have gone up to my goddamn room after banging her.  But whatever, I was retarded and still learning the ropes to this stuff.

So anyway, I could tell that she was starting to like me and playing these games to try to get me more attached to her, and then I ended up banging one of her best friends.  As described in the last post I linked to at the top.

She found out, and basically gave me the dirtiest looks I’ve ever received in my life for the next two years. It was pretty terrible.  I actually felt pretty bad, because that bitch could be seriously scornful… and she was one of my pretty good friends while that was going on.  It sucked.

Soooo I guess the moral of the story, similar to the last story, is not to fuck around with girls who are best friends unless you really don’t care about never seeing them again.  Argh.

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So it was sophomore year of college and my best friend D had met this freshman chick the first couple weeks that we were there.  He started hooking up with her, and we got to be friends with all these freshman kids that lived on her floor (we were all in the same dorm).  So we were going out with these kids all the time, partying like crazy, getting blackout drunk and making terrible decisions.  Making out with multiple chicks at the same time in basement frat parties and doing all the dumb shit that college kids do.  It was a fucking blast.

D started getting a little more serious with this girl over the next couple months, and they became official boyfriend/girlfriend status and everything.  Now I was also becoming good friends with his girlfriend, and I was hooking up with her best friend (who will be in the next post).  It was a pretty crazy environment where everybody was flirting with everybody else and hooking up all the time and all I was concerned with was fucking anything that walked, as fast as I possibly could.

I finally started feeling like I was getting to be a real pimp and starting to see some good success with the pickup artist stuff I’d been studying for almost a year at that point.  However, I still was at this point of extreme emotional immaturity where I didn’t really have confidence in myself to pull a lot of hot girls, so any chance I got I would take.

So basically, there was a lot of sexual tension that had always existed between myself and D’s girlfriend.  It tends to happen between a girlfriend and any guys around because that’s just how sexual tension works.  If there are barriers that wouldn’t allow you and a girl to hook up (another great example is two people who work together.. which is why people who work together are always hooking up secretly) then it just seems safer for the two of you to flirt with each other, because it’s all “safe” … or something.

But then you introduce extreme amounts of alcohol into the mix, and the fact that we were like 19, and what do you get… barriers that are broken down.  Also, I’m a complete douche and I made a serious mistake.

So, one night I was extremely drunk and so was D’s girlfriend, and D was nowhere to be found.  So we started talking about some shit and getting closer to each other and talking about how much we like each other and then she blew me.

And at that point I was basically in kill mode, and decided that I had to have her completely and fuck her.  I realized consciously that this was a terrible thing to do to D, but I guess I just didn’t give a shit, or understand the value of a friend over some dumb bitch.  So the next night the same thing basically happened (because we drank to near blackout pretty much every night) and I ended up fucking her.

It was good sex, very emotional obviously and very forbidden.  But it was not worth it.

The next day she ended up telling some people because she felt too guilty about it, and for the most part I lost a lot of friends out of that group of people.  So did D, because as it turned out, one night while his girlfriend was passed out in the same bed as one of her other best girl friends (who happened to be a total whore), he got in bed with them and had sex with his girlfriend’s friend.  While his girlfriend was in the same bed, asleep. HA.

So basically we were both fucked, and though D was quite pissed at me for banging his girlfriend, everybody else was more pissed off at D for pulling off such a ridiculous act of infidelity.  So D and I both are hated by about 10-15 people in that dormitory now, though I haven’t really seen any of them in a while.  But we got a pretty bad reputation for being total scumbags.

This really sucked because I lost some good guy friends on that floor out of the deal, and I also lost the trust of my best friend, though we ended up working it out after a while and becoming pretty good friends again.

For the record, that shit’s just not worth it.  This for me is the ultimate example of not shitting where you eat.  You have to have boundaries in your life.  Hopefully I’ll never make a mistake like that again.

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But about a year later that girl had joined a sorority and invited me to go with her to some kind of date night. I was down, thought I might get to fuck her again and if not I’d meet some of her sorority sisters.

Now I don’t remember why at this point, but for some reason she also had another date going.  It was a guy I was pretty cool with and had known from being on the crew team together a few years earlier.  So whatever, it wasn’t a big deal because I was still really just going to try to meet some of her sorority sisters and try to bang them out.

Before I went, it was necessary that I get extremely hammered because I didn’t know most of the girls in this sorority yet, so I didn’t want it to be awkward.  So I loaded up on Everclear and Amp energy drink before I went.  This is a recipe for blacking out.

The event itself was held at a bar, and about an hour into the event all I can remember is me sitting on a barstool passing in and out of consciousness due to extreme alcohol intake.  My date was nowhere to be found, and I was basically just hanging out with one of my roommates who happened to be going with another girl.

Later that night I got a call from my date who apologized for dipping out, and asked me if I wanted to come over to her place.  I said, sure why not.  Sounds like a solid invite to fuck.

I got there, and we started hooking up.  But she kept saying she had to go to the bathroom and disappearing for like 5 minutes at a time.  It was really weird.  Like, I kept getting down to her pussy and ready to fuck, and then she’d miraculously have to go to the bathroom again.  I thought she was like fucking with me or something.  After waiting another 5 minutes and being thoroughly pissed off with blue balls, I decided that “fuck it” I’m just going to peace out before she gets back from the bathroom.

I went home and told my roommates about the baffling disappearances into the bathroom… I was thoroughly confused, and pissed because I was still horny.

So, the next day I ran into the dude who was her other date.  We talked about what happened the night before, I told him I basically didn’t remember most of it because I was blacked out.  He told me that he ended up leaving early with her and banging her out at her apartment.

No shit.  I told him that she invited me over later to fuck but that some weird shit was going on so I ended up peacing out.  Good thing too, I didn’t want to be that guy’s sloppy seconds.  What a whore!

So THEN I come home and my roommate tells me that he talked to my date’s roommate, who said that my date was on her period yesterday and ended up getting a tampon stuck in her vagina.  Is that even possible?

So basically what we pieced together was that the other guy (who was a very big dude) must have banged her and trapped her tampon inside her pussy, which might explain why she kept disappearing to the bathroom when I was there.

Bottom line, that chick was a sliiiizzzzzuuttttttttttt!

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One night we were all hammered and hopping from one house party to another, and D’s older sister told me that I should try to hook up with her friend.  Her friend was a little indian girl with a cute face and a pretty tight body.  I was definitely down.  I just wanted to fuck anything.  I was horny as shit.

“Great, let’s do it” I said.

She went off and started chatting giddily with her Indian friend.  Sweet… I knew all I had to do was play it cool and not really mess anything up.  D’s sister was doing all the leg work for me.

We got back to their house, and the indian girl and I ended up awkwardly hanging out in her room.  I was still very unsure of myself, so basically I was scared to make the right move when the time came.  I found myself sitting on her bed at 3am strumming her acoustic guitar and pondering how I could make a move on this girl without embarrassing myself or getting rejected.  I was ultimately concerned with not looking like a creep, and with not getting rejected.

She sat down on the bed next to me and we were kind of touching shoulders. I thought to myself.  “Fuck, this is it.  I have to make a move now or forever be held in creepy friend status.”

I looked over at her and said “Hey.”  She looked up, I met her eyes and kissed her.  We started making out pretty heavily, then she got up to close the door and turned the lights off, and we fucked.  That made her the sixth woman I’d slept with.  Awesome.

Three years later, I was talking to my cousin who went to the same school as us and was the indian girl’s age.  It turns out that her future boyfriend was his future roommate, and my cousin hated this dude with a serious passion.  So when the guy really pissed him off one day, my cousin responded with a one-liner text message that was pretty good.  “Yeah?  Well, my cousin fucked your girlfriend.”

Boooooom.  I’m glad when my sexual exploits spread cheer throughout the world

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You see, my freshman year I was an idiot and decided to live in the honors student dorms.  Which basically meant, I was surrounded by nerds and the least hot girls I could have asked to be surrounded by.  Also, my roommate was completely boring and never partied at all.

Sophomore year, I was going to be living with my best friend from high school (we’ll call him D.) D was a menace to society, and had already banged a ton of girls.  Way more than me, that’s for sure.  He was a true natural.  So I knew it was going to be a much wilder year than the one before… and I was absolutely right.

So the first week that we were hanging out at school, D meets some freshman girl in a cafe across the street from our dorms.  She’s this extra-hot little spanish girl with a nearly perfect body.  She was about 5 foot nothing, probably around 100 lbs, and C or D-sized titties.  Cute face, tight little ass.

And she was really chill.She’d just broken up with her boyfriend who’d been with her through all of high school, and she was down to have some fun.  Awesome.

So the night that he met her, D invited this girl over to smoke week in our dorm room.  The three of us took some shots of jack daniels and went wandering around campus.  It seemed like she was into both of us, though D had dibs on her since he was the one who met her and everything.  So I ended up hanging out in somebody else’s dorm that night.

Later that night I come home and he told me that he banged her out after I left.  Excellent work, D.

Now a couple nights later, she ended up coming over to hang out again and for some reason D went off to do something else, so I was hanging out with her.  We were flirting and taking shots in my dorm room, and I definitely felt like I could make a move, but it felt weird because D had already banged her earlier that week.

So I’m kinda dragging my heels, and it starts to feel kinda weird, like when that window of opportunity is about to pass you by.  And then she comes out with this:

“So, you wanna have sex?”

Wow.  Holy shit.  Am I in a movie?

“Uhh.. Yeah.  Definitely.”

I was fucking nervous as hell.  HAHA.

So I just walked over to her and we started making out.  We took our clothes off, and I banged her out.  Her titties were some of the most amazing, perfectly shaped, perfectly 18-year-old giant boobies on a tight frame style tits I’ve maybe ever seen.

The sex wasn’t all that great.  I was pretty inexperienced at that point and definitely didn’t know what I was doing.  But who gives a shit.  Watching those titties bounce around was wonderful…

Then we put our clothes back on and walked out of the room to go do something else.

God bless college girls.

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So it turns out that they were both staying at the redhead’s place that night because her parents were away.  Perfect!  We brought over some wine and the four of us started drinking and watching tv and just hanging out.

Well, my buddy ended up drinking so much wine that he passed out.  Also, the asian girl went into a bedroom and it seemed like she was going to sleep too.

It was me and the redhead left awake, and I started getting a little physical with her on the couch… we started making out, then went to her room.  Sweet.  However, she wouldn’t let me get into her pants, and when I tried to get her to blow me she said that she has some weird condition where her jaw won’t expand.. like lockjaw or something.  I was like, what the fuck you’re clearly lying.  But she stuck to the story, so… whatever.

I sucked on her giant tits for a while and kept trying to get into her pants, to no avail.  Dammit.

I decided to go to the bathroom.

On my way there, I passed the asian girl’s room and decided to see if she was awake.  I walked in.

“Hey.  You awake?”

“Hi.  Sort of.  What’s up?”

“Umm.. nothing.  Just kinda bored.  I’m still up drinking.  Drink more!”

I sat down on her bed and put my arm around her while handing her my glass of wine.  She took a sip.  I looked at her and went in to kiss her.  She kissed me back.

We started hooking up pretty seriously.  I took her shirt off and sucked on her tiny asian nipples.  I grabbed her firm asian ass.

She was putting up no resistance.

I started fingering her.  I took her pants off.  I fingered her more and made out with her.  I sucked on her titties more. I put a condom on.  We had sex.

We talked afterwards while holding each other.  I actually kind of liked this girl.  I’d known her for a long time and we’d always flirted back and forth.  And finally, almost 6 years after we first met, we fucked each other.

I was hoping that we could turn it into a regular thing.  That would be pretty awesome.  She was hot.. even though she went to school a few states away, and school was starting up again pretty soon.

We fell asleep.

In the morning, I could see the two girls talking to each other.  I knew what they were discovering.

They weren’t really in the mood to talk after that.  My friend and I left.

The next semester I found out that she had transferred to an extremely strict christian college where religion was a major part of the curriculum.  The kind of school where kids don’t drink or do drugs, they just sit around talking about God all the time.  Later that year, I checked her facebook and she was dating this 90-pound balding kid who wrote lovey-dovey messages on her facebook wall every day.

Two years later, after graduating college, I checked her facebook wall again.  She had just married the dude and now she had all these pictures of herself with these SMOKING HOT women around her.  What the hell was that about?

After some further research, I found out that she’s now a cheerleader for an NFL football team.

So… boo-ya.  I fucked an NFL cheerleader.

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Now, my best friend from high school (we’ll call him Dex) was living on a nearby campus and having a lot of fun party times.  So I decided to start hanging out with him more and getting out there and meeting people.  He was a real natural with girls, so it could work well that we were both now single.

One night we ended up going to a concert with a girl who lived in his dorm, and her friend.  He was making his moves on the friend, and I had my eye on the girl who lived in his dorm, though she was slightly less attractive than his girl.  She was like a 6.5 out of 10, but I thought she had nice eyes.  Whatever.

So I talked to this girl a little at the concert and she seemed to be into me, but I wasn’t sure.  I was very nervous and never wanted to make the move myself, even though my pickup artist gurus all wrote about the importance of leading and making the moves.

So nothing happened the night that I met her, but I had her in mind and I knew she lived on the same floor as my buddy Dex, so I’d probably run into her again.

The next week, I went to visit him at his dorm to drink with some of his friends, and indeed she was there.  I was really awkward, but kept catching her eye and talked with her a little bit.

I was nervous.  I kept taking opportunities to talk with her about whatever I could think of, and we were both drinking so that definitely helped things along.

I ended up hanging out in her dorm room still trying to make conversation.  I was not very good at making random conversation back then, in fact I remember it feeling very awkward with lots of pauses.

The whole time I was thinking about opportunities I could take to try to make a move on her, but I just didn’t know how to do it.  I saw this weird coiled metal thing sitting there, so I asked what it was.

“It’s a head massager” She replied.

“Really?  How does it work?”

“Here, I’ll show you!”

She put this weird thing on my head, and it was awesome!  It scratched me in the most delightful way.  I wanted one.

“Wow that’s seriously amazing.  Let me try it on you.”

So I put the thing on her head and she made delighted sounds, and I thought, SHIT I need to make a move right now.  This is the time, we’re doing something kind of sensual.  I must man up and do this right now.

And with that, I went to make out with her.  And to my delight, she was all about it.

We started furiously making out and groping each other.  I turned off the lights, we got under the covers, and after a few minutes of further groping, I asked her if she had a condom.  She got one, and we banged.  Third girl I banged ever! Woo!

Afterwards, I was no longer so interested in hanging out with her.  She did not seem nearly so attractive afterwards.  Hmm, interesting.  This is the first girl I banged who I wasn’t in love with when I did it.

I felt good though, like I’d just conquered something.  I felt like more of a man.  I wanted more of this… probably not with this girl, but with lots of others.  And I would get what I wanted.

I put my clothes on, and went down the hall to the bathroom.  I washed my hands and stuff, and then went back to hanging out with my friends.

I never really talked to that girl again.  I felt really awkward whenever I would see her around and I’d divert my eyes.  Every so often I’d see her on the college buses or something for the next 3 years, but never said a word.  She put on a couple pounds in the coming years.  Oh well.

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I was a pretty good-looking guy, and I sat at the “cool kid” table, so there were some girls that were definitely interested in me.  As I’ve said before, my school was tiny with only about 60 kids in each grade.  So the social scene was well-defined.

So I was considered pretty cool by default, but for some inane reason I was deathly afraid of screwing up my reputation.  The fact was, I stayed quiet because I felt inside like I wasn’t that cool of a kid.  So by staying aloof and not talking to the kids who were in the younger grades, I probably got a reputation of being a snob or something.  Which I was fine with, so long as my status was above theirs.

However, it all felt like kind of a sham to me.  I knew I was just nervous about acting like a fool, and my ego couldn’t take rejection if I hit on some of the younger girls and they didn’t reciprocate.  Plus, I didn’t really know how to talk to girls for the most part.  So for the majority of my time in high school, I just talked to kids in my grade, and didn’t really get any play at all.

I never put myself out there.

Now, senior prom was coming up, and I didn’t have any idea who I was going to bring.  But it was important to me that I bring a hot girl.  After all, I was very concerned with my reputation.  I had to make something happen.  The year before I’d brought a cute asian chick to junior prom (who will get her own awesome post in the future, but we’ll save that for later…) and this year I had to bring an even hotter girl.

I looked around the lunch room… who could I bring?  Who in this school was the perfect target, both highly attractive and didn’t have plans for prom?  Well, most of the juniors and seniors were already spoken for, or not hot enough.  And there weren’t many cute girls in the sophomore grade at all.

That left the freshmen.  There were actually a lot of cute freshman girls, and they were obviously not spoken for.  It was very tempting.  Most of us guys would sit around and comment on all the girls most days, and the freshmen were constantly drawing our attention in one way or another.  It was pretty scandalous though, because they were like 15 and I was 18 by now.  But fuck it, I said, these girls really were way hotter than the other girls in our school.  And there was one in particular that I’d had my eye on all year but never spoken to.  So why not.

Now, I was scared shitless.  I not only was going to talk to this girl for the first time, but I was also going to ask her to prom.  That’s not only weird and awkward, it’s creepy.  But fuck it, I said.  I have to do this.

This next part might surprise you.  Actually, typing it out is very embarrassing.  You’d think a guy who’s banged over 60 women would be a little smoother than this.  Nope.  I was not always good with girls, to say the least.

That night after school, I got her AIM screen name from a friend of hers and sent her a message to start chatting with her.  I wish to god I still had this conversation saved, because it would probably be the most entertaining and awkward thing than anyone could ever read.  Epic FAIL.

Basically, I said who I was, she obviously knew of me because it’s a small school… and then I said that I needed somebody to come to prom with me and I thought she was cute so I wanted to know if she had any plans.

HAHA.  I asked a girl to prom over instant messenger.

She said she had to ask her parents if it was OK to go, but that she was interested.  So I said OK, and waited, and then she came back and said she probably could.

Amazing.  I was extremely excited.  Despite the fact that it now seems really creepy that I was 18 and she was 15, I had a pretty big crush on this girl, so I was psyched.

The next day in school, I was still too embarrassed to actually talk to her in person.  Yes, that’s right, it took me another 2 days to actually talk to her in person.  Weirder, creepier actions could not be made, my friends.  But she was still down for it.  Eventually I went and talked to her for a little bit in the hallway and I was so nervous I didn’t think I could breathe, or something, but I did.

Since we were going to prom, we decided we should get to know each other beforehand (no shit).  So we made a date for her friends and my friends to go to a coffee shop or something and just hung out.  We ended up hanging out a couple times before prom, and it was going pretty well.  I was completely smitten by her.

Then prom rolled around and we went, and I danced with her and finally kissed her that night.  It was awesome.

We continued dating after prom, and I would drive to her town all the time and pick her up and we’d go to starbucks or something and hang out, then maybe drive into some deserted street and hook up in the back seat.  I got head a couple times I think.

I made her mix tapes.

I wrote her a song on guitar using basic chords.

Yes, I was in love.  The cheesiest, gayest love in the world.

August rolled around, and I was still in love but had to go away to college.  I decided that I liked her so much it didn’t matter, we could do long-distance dating and I’d come home every other weekend or so.

TERRIBLE PLAN.  Anyone reading this in high school, dump your fucking girlfriend before you leave for college.

My first semester of college was spent mostly not making friends and instead talking to her on the phone and whining about how I missed her.  And sometimes coming home to meet up with her.

One time I came home to meet her at a high school party with a lot of her friends from our school. Everybody was drinking, and we ended up finding a condom and she seemed excited about the idea of having sex.  So we found a room, and we started hooking up, and then I put the condom on and I took her virginity.  Girl #2.

It was the worst sex ever.  She was in pain the whole time, and afterwards she started crying.  It was terrible.  It turned out that she regretted doing it, and since she was upset I also deeply regretted it now.  There was nothing I wanted more than for her to be happy, and the thought that I had made her upset was just terrible.  I had no idea how to be in a relationship.  I was a fool.

So we continued talking on the phone every day after that and hanging out.  But I was an hour away at college, and the most I could see her reasonably was about every 2 weeks.  Meanwhile, she was getting more and more bored with my constant whining about how I missed her and loved her sooo much bla bla bla.  She was like 16 by now and these girls have ADHD.  It’s ridiculous, I was retarded.

So for Valentine’s day I bought tickets to a comedy club and bought her a necklace with a heart on it, and brought her out.  And she started a fight with me about some bullshit and we didn’t talk the entire time, and then we broke up.  Fuck.

7 months of dating this girl. I felt like there was a knife in my heart.  As bad as my first breakup was with the 21 year old, this was many times worse.  I had invested so much more time and effort into this relationship.  I had decided that she was the one.  I was fucking WRECKED.  All my brilliant plans laid to waste.

I cried for fucking days.  DAYS.  This was not going to go away easily.  In fact, for years after this girl I still had awful thoughts when I pondered what happened, how I had failed.  How I’d lost my damn princess.

Just writing this right now is getting me choked up, and this was five years ago.

I was left with nothing.  I hadn’t made many friends at school, I poured all my energy and love into this girl, a girl not even close to old enough to appreciate the amount of effort I was putting in, a girl who it probably wasn’t even legal for me to be dating, and now I had lost even that.  Pathetic.  I was in a new social environment with a bunch of kids I barely knew, and now I felt completely alone and abandoned.

This is probably the worst feeling I can remember from my entire life.  It sounds stupid, considering how much awful shit happens to people, that getting broken up with when I was 18 is the worst thing that’s happened to me, but I really think it might have been.  The feeling of loneliness and not having any of my friends who I grew up with was almost too much to bear.

What the fuck was wrong with me?

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Now everything seemed to be going along swimmingly.  I finally had a serious hookup with this chick that I’d been chasing after for a couple months by now, and fantasizing about  for most of my teenage years.  I really liked this girl a hell of a lot, and all was basically going according to plan.  But some there are some things you should know.

1. This girl still technically might have a boyfriend, but I dared not ask about him.  I just went under the assumption that if we were spending so much time together and being so passionate, that he would just sort of, um, disappear.  And that didn’t seem too preposterous, because to my knowledge, the way she had started dating this guy was by cheating with him on her prior boyfriend, another friend of ours.  So, I thought, maybe this could work out.
2. This girl turned out to be fairly interested in cocaine.  I did not like it because at that age, all I really knew about drugs like cocaine were “drugs = bad.”  Now, at this point in my life I still have never done coke, but I would probably not be quite so concerned about a 21-year-old friend experimenting with a little cocaine from time to time.  Hell, it’s their life.  But back then, this coke thing concerned me quite a bit.  I was frightened that she would get addicted, and it was a growing concern of mine.  She said that she had only done it a few times, but I had my suspicions.
3. We still were not telling anybody about this.  Not our friends, not my mom, nobody.  I told a couple of my friends at school who were unrelated though because I thought it was sweet that I was hooking up with an older girl.  And they were duly impressed.  But my mom was growing more and more suspicious of me taking the train into the city so often, and I was getting more and more frustrated with her prying.

So I’m somewhere right around my 17th birthday, and I’m now taking the train into the city every other weekend to hang out with this love of my life.  I’d go to college parties with her and drink wine and beer and Jameson and we started having regular sex.  I’m pretty certain that I lost my virginity in the back of her (and I’m guessing as to the year here) 1990 Toyota Corolla while I was hammered.  Considering that I don’t really remember the exact event, I’m pretty certain that I was.  Because that’s the kind of thing most people remember.  But I don’t regret it, because I was having fun and I liked her quite a whole lot.

We had really dirty sex.  She had a kinky mind, and so did I. We’d push each others’ boundaries, and we’d say really dirty shit to each other.  Sometimes we would have phone sex, one time I remember fingering her while she was driving down the garden state parkway, and another time I even fucked her in the ass.

Banging her in the ass was awesome.  I enjoyed the feeling of power that came along with it.  They have to trust you, because if you do it too hard or too fast, you can really hurt them.  And aside from that, it’s extremely taboo.  As you will see, this begins a trend that continues in my later sexual conquests.

So anyway, we’re doing this stuff every other weekend and sneaking around and lying to everyone and it’s going quite swimmingly, until I started to get some strange signs from her.  For one thing, she wasn’t coming online as often to chat like she used to.  And then when I’d come up to visit, she might not be around the entire time or she would leave me hanging out with our other friends who lived in her apartment while she was off doing random stuff.  And we just didn’t have quite as much to talk about as we used to.

I guess you could say that the initial phase of rapid, lustful interest was slowing down after we’d been sort of  seeing each other for a number of months and we were hitting that point where a relationship might grow a little more mundane.  Or something, I don’t really know how it works to be honest.  I don’t have hardly any experience with long-term relationships.  This is just what I’ve heard.

But essentially, I think she just got a little bit bored of me.  She was a conqueror, after all, just like me.  And when things slow down, a conqueror moves on to the next thing.  I was not wanting to move on, in fact I was perfectly content and absolutely in love.  But I could tell that her interest was waning, which broke my heart.

And then one day I came back to her place and I saw some used condoms in her trash, and… I know, I know. I’m devoting myself to pure honesty here… I started bawling.  Like a fucking post-menopausal woman, I started crying and told her that I could tell she didn’t like me like she used to and now I knew she was fucking other people and my life was essentially over.

And she held my head in her boobs and said things like “Oh, jesus” and “Look, those are condoms we used the last time you were here.  [Her boyfriend] and I don’t even use condoms.”  Which may very well have been true, I have no idea.  But either way, I was a fucking hysterical mess and the relationship was basically doomed at that point.

Then I found out that she did coke again the following week, and I got extremely upset with her.  And I decided that it was time to make things official so that she didn’t have to.  I wanted to save my last shred of dignity.

I drafted an email to her explaining my feelings, and telling her that I still loved her, but that I had to end it because I didn’t think it could work any more, and I was scared that she was with other people, and I couldn’t take that anymore.  And also that I was scared about her cocaine abuse.  I took my time with this letter, and as I was writing it I was crying.

And as I was finishing the email, my mom walked into my room while I was all red in the face, and she saw the word “love” on the screen, and she started going insane and screaming at me about how she was scared of what I was doing when I was taking the train to NYC every other week, and how she knew that I was dating this girl, and that she didn’t like it because she was so much older than me.

And finally, once I had screamed her out of my room, I was now pissed off because my mother of all people had just interrupted the drafting of my farewell letter.  I didn’t want my mom to know anything about my emotions, particularly this in my weakest of moments.  I was so fucking pissed off.

I finished the email and I sent it off.  And I was left with this horribly horrid horrible feeling that I was 17 years old and hated everything about my life.  The one girl who I focused all my positive emotions into had just been cut out, and I deeply resented my mom, and I didn’t have that many close friends at school at that point… and I hated everything.  Everything.  College was over a year away, and I didn’t know how I was going to manage living in this hellish parented and high-schooled existence for another year and a half.  I was shredded into pieces, hopeless. And I cried some more.

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